Fact-checked by Grok 2 weeks ago

Borneol

Borneol is a bicyclic monoterpenoid with the molecular formula C₁₀H₁₈O and the IUPAC name 1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, existing naturally as two enantiomers: (+)-borneol (d-borneol) and (−)-borneol (l-borneol), while synthetic borneol is typically the . It features a camphor-like and a burning, mint-reminiscent , with physical properties including a of 202–209 °C, a of 210–212 °C, and low water solubility of approximately 0.74 g/L at 25 °C. Chemically, it is flammable and serves as a chiral building block in , often derived from the reduction of . First identified in 1842 by French chemist Charles Frédéric Gerhardt as "camphre de Bornéo" from Borneo-sourced resins, borneol has been extracted historically from the essential oils and resins of aromatic plants and trees. Its primary natural sources include the Borneo camphor tree (Dryobalanops aromatica), cinnamon species such as Cinnamomum burmanni and Cinnamomum camphora, and various essential oils from plants like rosemary (Salvia rosmarinus), ginger (Zingiber officinale), and frankincense (Boswellia sacra). Industrially, natural borneol is produced through steam distillation of these sources, while synthetic versions are produced from α-pinene (derived from turpentine) through isomerization to camphene, esterification, hydrolysis to isoborneol, and isomerization to borneol, or by reduction of camphor to isoborneol using agents like sodium borohydride followed by isomerization, addressing supply shortages of the natural product. Borneol holds significant applications in traditional Chinese medicine (TCM), where it is valued for its anti-inflammatory, analgesic, and blood-circulation-promoting properties, often used to treat conditions like pain, inflammation, and cardiovascular disorders. In modern contexts, it functions as a penetration enhancer for across the blood-brain barrier and mucosal tissues, improving the efficacy of therapeutics. Additionally, borneol is employed in perfumery and flavoring for its camphor-like, piney scent, appearing in fragrances, food additives, and products like rosemary-seasoned seasonings, though it requires careful handling due to its irritant potential and flammability.

Structure and properties

Chemical structure

Borneol is a bicyclic monoterpenoid with the molecular \ce{C10H18O}. Its core structure is based on the bornane skeleton, which is a bicyclo[2.2.1] system featuring at position 1 and dimethyl groups at the one-carbon bridge (position 7). A hydroxyl group is attached at the 2-position on the two-carbon bridge, defining it as a secondary . The systematic IUPAC name for the endo isomer, which is the predominant natural form, is (1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol. In bond-line notation, the structure is depicted as a fused ring system where carbons 1 and 4 serve as bridgeheads connected by two two-carbon bridges and one direct bond, with the hydroxyl oriented endo (toward the larger bridge) relative to the two-carbon bridges. The 3D representation of the bornane skeleton shows a rigid, envelope-like conformation similar to norbornane, with the C7 methylene bridge protruding above the plane formed by the bridgehead carbons and the two-carbon bridges, imparting strain and influencing the molecule's reactivity. The compound was first isolated and named by French chemist in 1842, who identified it as "camphre de Bornéo" from the resin of the tree Dryobalanops aromatica.

Physical and chemical properties

Borneol appears as a colorless to white solid, typically in the form of lumps, crystals, or powder, and possesses a pungent, camphor-like . Its is 154.25 g/, with a of 1.011 g/cm³ at 20 °C, a of 202–204 °C, and a of 210–212 °C. Borneol exhibits low solubility in water (approximately 0.738 g/L at 25 °C) but is readily soluble in organic solvents such as , , and . Under normal ambient conditions, borneol is chemically stable, though it is flammable and reacts with strong oxidizing agents to form . The enantiomers display optical rotations of +37° for d-borneol and -37° for l-borneol (in ethanol solution). In infrared (IR) , borneol is characterized by a broad O-H stretching band at approximately 3400 cm⁻¹, indicative of the . Key features in ¹H () spectroscopy include the methine proton adjacent to the hydroxyl group at around 4.0 ppm (multiplet), distinguishing it from the isoborneol . of borneol shows a molecular peak at m/z 154, with the base peak at m/z 95 resulting from loss of water and rearrangement.

Isomers and stereochemistry

Borneol possesses three chiral centers located at carbon atoms C1, , and C4 in its bicyclic structure, which theoretically permit up to eight stereoisomers; however, the rigid camphane skeleton restricts viable configurations, resulting in four principal stereoisomers consisting of two pairs of enantiomers for the and forms. The at is particularly significant, defining the endo orientation of the hydroxyl group in borneol versus the exo orientation in its , isoborneol. These diastereomers share the same connectivity but differ in the relative spatial arrangement at , exemplified by the (1R,2S,4R)-configuration for (+)-borneol and analogous adjustments for its counterparts. The enantiomers of borneol are (+)-borneol, also denoted as d-borneol with the (1R,2S,4R), and (-)-borneol or l-borneol with (1S,2R,4S). Similarly, isoborneol exists as (+)-isoborneol and (-)-isoborneol enantiomers. In chemical synthesis, particularly via reduction of racemic , mixtures often yield racemic borneol alongside isoborneol, complicating separation due to similar physical properties. In nature, both enantiomers occur, with (+)-borneol sourced from plants in the family, such as Dryobalanops aromatica, and Valerianaceae, including species. The (-)-enantiomer predominates in essential oils from families like Compositae, Graminaceae, and Labiatae. This natural distribution often results in optically impure extracts, where the enantiomeric excess influences bioactivity; for instance, (-)-borneol has been shown to exhibit distinct immunomodulatory effects on neutrophils compared to its counterpart.

Occurrence and production

Natural sources

Borneol occurs naturally as a bicyclic primarily in the essential oils of various , where it contributes to their aromatic profiles and biological activities. The compound exists in both (+)- and (-)-enantiomeric forms, with natural sources yielding predominantly the D-(+)-borneol in certain species. Among the most significant plant sources is the Borneo camphor tree, Dryobalanops aromatica (), native to and classified as vulnerable due to for its , from which borneol can constitute up to 30% of the resinous exudate , though concentrations as high as 68% have been reported in oils. Other notable sources include Cinnamomum camphora (), particularly the borneol chemotype, where borneol levels in s range from 16% to 85%, depending on the variety and region. In Blumea balsamifera (), a widespread in , borneol comprises about 1-23% of the , serving as a key source for (-)-borneol extraction. Additional plant sources include Heterotheca inuloides (Asteraceae), known as Mexican arnica, where L-borneol is a major component in the flower and leaf essential oils from North and Central American species. Borneol is also present in essential oils of Artemisia species (Asteraceae), such as A. herba-alba and A. argyi, at levels of 5-18%, contributing to their medicinal properties in Mediterranean and Asian flora. Rosemary (Rosmarinus officinalis, Lamiaceae), a Mediterranean herb, contains borneol at 1-16% in its leaf essential oil. Similarly, the rhizomes of Kaempferia galanga (Zingiberaceae), an aromatic ginger from Southeast Asia, yield essential oils with 2.7-5% borneol. Geographically, borneol-rich plants are concentrated in , exemplified by D. aromatica in and , and C. camphora and B. balsamifera across , , and , though species like R. officinalis extend its distribution to the Mediterranean and H. inuloides to the . Trace amounts of borneol (0.1-5% in oils) have been detected in some fungi and insect exudates, but these are minor compared to plant-derived sources. Borneol is typically extracted from these natural sources via of leaves, resins, or rhizomes, a method that preserves its volatile nature and yields essential oils for further purification. Historically, borneol from D. aromatica was traded as "Borneo " from to and since ancient times, valued for its medicinal and preservative qualities. Biosynthetic enzymes like bornyl diphosphate synthase facilitate its production in these .

Biosynthesis

Borneol is biosynthesized in and microorganisms through the pathway, beginning with the condensation of (DMAPP) and isopentenyl pyrophosphate (IPP) to form (GPP). GPP then undergoes cyclization to bornyl pyrophosphate (BPP) catalyzed by bornyl diphosphate synthase, followed by of BPP to yield borneol. This pathway operates within the mevalonate (MVA) or methylerythritol phosphate (MEP) routes, depending on the organism, and is regulated as part of broader metabolism. Key enzymes in this process include monoterpene synthases such as (+)-bornyl diphosphate synthase, which facilitates the metal-dependent of GPP to (3R)-linalyl diphosphate and subsequent cyclization to (+)-BPP with high specificity. For instance, in , the enzyme produces (+)-BPP as 75% of its product from GPP. The subsequent dephosphorylation of BPP to borneol is mediated by , such as Nudix hydrolase WvNUDX24 in Wurfbainia villosa, which initiates the step and influences borneol accumulation. Similar synthases, like CbTPS1 from burmannii, exhibit kinetic parameters including a K<sub>m</sub> of 5.11 μM for GPP, underscoring their role in directing flux toward bicyclic monoterpenoids. Genes encoding these have been cloned and characterized, providing insights into regulation. In S. officinalis, the (+)-bornyl diphosphate gene corresponds to cDNA clone 3C6 (: AF051900), expressed as a homodimeric protein that stabilizes intermediates via cation-π interactions during cyclization. Expression of such is modulated by environmental factors and integrated into the MVA pathway, where upstream enzymes like influence precursor availability. In C. burmannii, the CbTPS1 (: MW196671) has been heterologously expressed to study pathway dynamics. Biosynthetic variations across species include differences in endo- versus exo-isomer production, with most plant synthases favoring the endo configuration of (+)-borneol through stereospecific PPi recapture in the active site. For example, BPPS from S. officinalis enforces endo specificity via structural constraints in its α-helical domains. Microbial engineering has enhanced yields by optimizing these pathways; in engineered Saccharomyces cerevisiae, co-expression of truncated BPS genes with MVA pathway modules and phosphatases increased (+)-borneol production by up to 96-fold to 2.89 mg/L. Further improvements, such as BPP dephosphorylation engineering, have achieved 33.8-fold titer boosts in yeast, demonstrating potential for scalable in vivo production.

Industrial synthesis

Industrial synthesis of borneol relies on chemical reductions and rearrangements, often starting from or pinenes derived from oil. In the early , processes emerged using as a feedstock, involving conversion of to borneol derivatives through acid-catalyzed reactions, enabling scalable production for commercial applications. Modern synthetic borneol achieves purity levels exceeding 98%, meeting pharmaceutical and fragrance industry standards. A primary method is the of , a common precursor. The Meerwein–Ponndorf–Verley () employs aluminum isopropoxide as a catalyst and isopropanol as a donor, converting to a of and isoborneol stereoisomers. This reversible process favors the exo (isoborneol) due to steric factors, typically yielding borneol in lower proportions within the mixture. Alternatively, (NaBH₄) of in also produces a borneol/isoborneol mixture, with the reaction proceeding via delivery to the , though it is more prevalent in laboratory-scale preparations than large-scale operations. Another established route utilizes the Wagner–Meerwein rearrangement from , abundant in . undergoes acid-catalyzed isomerization to , followed by hydration or esterification to form isobornyl derivatives, which are then hydrolyzed to borneol. This pathway, involving migrations, supports efficient industrial conversion with high from renewable sources. Recent advancements focus on biocatalytic methods for enantioselective , addressing limitations of chemical routes in stereocontrol. Engineered Saccharomyces cerevisiae expressing bornyl pyrophosphate synthase and pathway enzymes produces borneol at up to 23 mg/L in two-phase , demonstrating potential for scalable microbial synthesis. Similarly, whole-cell biocatalysts with engineered reduce (+)- to (+)-borneol under mild aqueous conditions (25 °C, 6.2), achieving 45% isolated yield and >99.5% diastereomeric excess on gram scales, suitable for high-purity pharmaceutical applications.

Chemical reactions

Oxidation reactions

Borneol, a bicyclic secondary , is readily oxidized to the corresponding , , through the loss of two atoms from the hydroxyl-bearing carbon at position 2. This transformation is a standard method for preparing and exemplifies the selective oxidation of secondary s to s without affecting other functional groups in the structure. The overall reaction can be represented as: \ce{C10H18O ->[oxidant] C10H16O + 2H} Common oxidizing agents for this conversion include (as in the Jones reagent), (), and the protocol. , typically used in acetone solution, provides efficient oxidation under mild conditions, yielding in high purity after . , introduced by and , operates in at and is particularly selective for secondary alcohols, minimizing over-oxidation risks in sensitive substrates like borneol. The , employing dimethyl sulfoxide (DMSO), oxalyl chloride, and triethylamine, also proceeds under anhydrous, low-temperature conditions to deliver with excellent yields and is favored for its compatibility with acid-labile groups. The for these oxidations generally involves initial activation of the hydroxyl group, followed by abstraction from the adjacent carbon to form the carbonyl. In oxidations, the coordinates with the (VI) species to form a chromate , which undergoes rate-determining elimination of a , regenerating the oxidant and producing the . For , the involves formation of a chromate , similar to oxidation, followed by elimination of a . For the , the pathway proceeds via a after activation of DMSO, ensuring clean conversion with retention of the bicyclic in the product, as the reaction does not alter the configuration at or other chiral centers. Mild conditions with these selective oxidants are crucial for borneol, preventing side reactions such as ring cleavage in the strained framework. This oxidation serves as a key intermediate step in the synthesis of various derivatives, where acts as a versatile precursor for further functionalizations, such as in the production of pharmaceuticals and fragrances derived from monoterpenes.

Reduction and esterification

Borneol can be produced through the reduction of , a related bicyclic , using aluminum () as the , which selectively delivers a to the , yielding the secondary borneol. This typically generates a of stereoisomers, borneol (endo configuration) and isoborneol (exo configuration), with the exo product often predominating due to steric factors favoring hydride attack from the less hindered face of the . An alternative synthetic route involves the partial of , a , to isoborneol, though this often proceeds via carbocation-mediated addition rather than direct transfer. Esterification of borneol is commonly achieved by reacting the with in the presence of an acid catalyst such as (H₂SO₄), forming bornyl as the primary product. This reaction follows the general mechanism of , where the hydroxyl group of borneol attacks the carbonyl of the anhydride, displacing . The balanced for this transformation is: \text{C}_{10}\text{H}_{17}\text{OH} + (\text{CH}_3\text{CO})_2\text{O} \rightarrow \text{C}_{10}\text{H}_{17}\text{OCOCH}_3 + \text{CH}_3\text{COOH} The acid catalyst protonates the carbonyl oxygen of the anhydride, enhancing its electrophilicity and facilitating the reaction, while also influencing ; in related additions, such conditions favor products due to the stability of the intermediate leading to the endo/ acetate isomers. This esterification preserves the stereochemistry of the starting borneol but can exhibit selectivity in mixtures of endo and alcohols. Bornyl acetate and related borneol esters find synthetic utility in the preparation of fragrances, where the compound imparts a characteristic piney, woody aroma used in perfumes, air fresheners, and personal care products. In pharmaceuticals, these esters serve as intermediates for derivatives exhibiting anti-inflammatory and antimicrobial properties, enhancing drug delivery or formulation stability. Note that esterification represents a reversible derivatization, contrasting with the oxidation of borneol to camphor.

Applications

Traditional and medicinal uses

In (TCM), borneol, known as Bingpian, is valued for its ability to clear heat, open sensory orifices, relieve pain, and serve as a carrier to enhance the delivery of other medicinal substances across biological barriers. It is classified as acrid, bitter, and cool in nature, entering the Heart, Lung, Liver, and Spleen meridians, and has been employed topically and internally for conditions involving , swelling, and neurological disturbances. A prominent example is its inclusion in the classical formulation Angong Niuhuang Wan, where it contributes to treating febrile diseases, coma, and disorders by promoting resuscitation and reducing heat. In Ayurvedic medicine, borneol, referred to as Pachha Karpooram, is utilized for its , , and properties, particularly to address respiratory issues such as and . Similarly, in medicine, borneol supports analgesia and mild sedation, aiding in the management of pain and calming effects in prescriptions adapted from traditions. Historically, borneol has been employed across Asian cultures as an aromatic , often called "dragon's brain ," for and to alleviate digestive distress and fevers. In 19th-century Western contexts, it appeared in remedies akin to camphor-based treatments for respiratory ailments, including , due to its qualities. Borneol is commonly administered in crystalline form or as an , with typical oral doses in TCM ranging from 0.15 to 0.3 grams per day for synthetic varieties, or up to 0.9 grams for natural sources, often divided into multiple administrations.

Industrial and modern uses

Borneol serves as a key ingredient in the fragrance industry, where it imparts woody, camphoraceous, and pine-like notes, particularly in the form of l-borneol used to enhance perfumes, soaps, and detergents. It is incorporated into fine fragrances, shampoos, toiletries, and decorative cosmetics at low concentrations to provide a cooling, balsamic undertone, often in formulations mimicking rosemary or lavender scents. In the food sector, borneol functions as a generally recognized as safe (GRAS) flavoring agent by the U.S. FDA, contributing subtle spicy or herbal profiles to products such as spices, nuts, and beverages, typically at trace levels to avoid overpowering tastes. As an , borneol is formulated into topical products targeting mosquitoes, including , due to its natural deterrent properties derived from essential oils. It appears in compositions at concentrations around 2-4% by weight, often combined with other like α-pinene for enhanced efficacy against biting . While direct synergy with has been explored in broader botanical repellents, borneol contributes to multi-component blends that extend protection duration. In modern , borneol acts as an in the combination edaravone dexborneol, where dexborneol (a form of (+)-borneol) facilitates penetration of the neuroprotective agent . The injectable form, Sanbexin®, received approval from China's (NMPA) in July 2020 for treating acute ischemic , marking it as a Class I innovative . A sublingual tablet version of Sanbexin® was subsequently approved by the NMPA in December 2024, offering improved neurological outcomes and functional recovery in patients with acute ischemic within 48 hours of onset. In August 2024, Sanbexin sublingual tablets received Designation from the U.S. (FDA) for the treatment of acute ischemic . Beyond these primary applications, borneol finds use in for its aromatic and soothing qualities in creams, lotions, and formulations, as well as in veterinary products where it enhances the of antibiotics like florfenicol for treating respiratory infections in animals.

Pharmacology and

Pharmacological activities

Borneol enhances the penetration of drugs across the blood-brain barrier () through a reversible, transient opening mechanism. Proposed mechanisms include alteration of tight junctions and downregulation of efflux transporters such as , thereby improving of co-administered agents like and nimustine. This property has been leveraged in to augment the delivery of therapeutics to the , facilitating targeted brain region access without permanent disruption to barrier integrity. In terms of and effects, borneol inhibits key pathways including COX-2 and , reducing proinflammatory release and mitigating inflammatory responses. Animal models of induced inflammation, such as for or , have shown borneol significantly decreases and pain behaviors by activating p38-COX-2-PGE2 signaling and disrupting TLR4/-mediated cycles. Borneol demonstrates moderate antimicrobial activity against bacteria like and fungi such as , primarily through disruption of cell membranes and formation. Minimum inhibitory concentrations (MICs) for these pathogens typically range from 0.5 to 2 mg/mL, with enhanced effects observed in combinations targeting preformed biofilms (33.7–58.2% inhibition at 0.25–4 mg/mL). Borneol provides neuroprotective benefits in ischemic models by reducing infarct and improving neurological outcomes, as evidenced by studies in rats where doses of 1.0 mg/kg decreased volume through anti-apoptotic and anti-necrotic mechanisms. Recent investigations from 2024–2025 highlight borneol's role in anti-influenza activity by inhibiting viral entry into host cells, particularly through modeling of borneol derivatives targeting replication. Clinically, the phase III TASTE trial (2021) demonstrated that dexborneol—a formulation incorporating the dextrorotatory of borneol—improved 90-day functional outcomes in acute ischemic patients compared to alone, with benefits linked to borneol's BBB modulation; this led to its approval in in 2024 and U.S. FDA designation in 2024. As of November 2025, full FDA approval is pending. Additionally, borneol exerts antioxidant effects by scavenging (ROS), inhibiting their generation in activated neutrophils and oxygen-glucose deprivation models to prevent oxidative neuronal damage.

Toxicity and safety

Borneol exhibits low acute oral , with an LD50 value of 5,800 mg/kg in rats. It may cause mild to the eyes and upon contact, as well as including to the and . Dermal exposure can lead to burns in severe cases, though borneol does not pose a significant risk for . High-dose exposure to borneol can result in symptoms such as , , , , and , potentially leading to loss of . While borneol modulates receptors, potentially contributing to neurotoxic effects at elevated levels, no evidence indicates carcinogenicity, and it remains unclassified by the International Agency for Research on Cancer (IARC). Mild may occur in sensitive individuals upon skin contact, but patch testing supports its safety at concentrations up to 5% in cosmetic formulations. Borneol is recognized as generally regarded as safe (GRAS) by the U.S. (FDA) for use as a agent. In the , it is permitted in fragrances and without specific concentration limits beyond general good practices, though fragrance allergens are restricted to 0.01% in leave-on products when declarable. As of 2025, no new findings on have emerged, confirming its non-genotoxic profile, and clinical studies support its safety in combination therapies for acute ischemic at doses including up to 37.5 mg of dexborneol (a borneol ) twice daily.

Derivatives and recent research

Key derivatives

Borneol, a bicyclic with the formula C₁₀H₁₈O, serves as a precursor for several key derivatives through modifications such as esterification, , and oxidation. These derivatives retain the core bornane skeleton and are prepared via or reactions on the hydroxyl group. The most common ester derivative is bornyl , formed by of borneol, with the molecular formula C₁₂H₂₀O₂. This compound features the bornyl group (C₁₀H₁₇-) esterified with acetic acid and is widely utilized in perfumes due to its balsamic, pine-like aroma. Bornyl chloride represents a key halogenated , obtained by of the hydroxyl group with , yielding the C₁₀H₁₇Cl. It acts as an important synthetic intermediate in chemistry, often prepared from borneol using or . Oxidation of borneol produces , a bicyclic with the C₁₀H₁₆O, where the secondary is converted to a . This is typically synthesized using oxidizing agents like or . Other notable derivatives include bornyl isovalerate, an with the formula C₁₄H₂₄O₂ formed by reaction with isovaleric acid. The bornyl group itself (C₁₀H₁₇-) denotes the univalent radical derived from borneol by dehydroxylation and is used in IUPAC for naming related compounds.

Emerging research applications

Recent studies have explored N-butylphthalide (NBP)/borneol hybrids as potential neuroprotective agents for ischemic , demonstrating enhanced blood-brain barrier (BBB) penetration compared to NBP alone. In a 2025 investigation, these conjugates exhibited superior neuroprotective effects in cellular models of cerebral ischemia by improving to ischemic regions and reducing neuronal damage. Similarly, borneol-based polymeric micelles have shown promise in facilitating intracerebral for pathogenesis-adaptive treatment of ischemic , with improved BBB crossing via transient modulation of tight junctions. In chemoinformatics research from 2025, newly designed borneol-phenolic diterpenoid derivatives were identified as potential inhibitors of influenza A virus entry, particularly against the H1N1 strain (A/Puerto Rico/8/34). These hybrids displayed favorable binding affinities to viral hemagglutinin, suggesting mechanisms that block viral attachment and fusion with host cells, with predicted low toxicity profiles. Borneol esters synthesized in 2016 have demonstrated anti-inflammatory properties, with certain derivatives reducing edema in animal models. Additionally, borneol has been shown to enhance the cellular uptake of curcumin, improving its photodynamic fungicidal efficacy against Candida albicans. Borneol-modified nanoparticles have emerged in preclinical trials as enhancers for delivery to tumors, particularly . For instance, borneol-gastrodin liposomes co-administered intranasally with () reversed drug resistance by inhibiting efflux, achieving higher tumor accumulation and improved survival in glioma-bearing models. Likewise, borneol-modified micelles loaded with and tetrandrine, in a 2024 study, targeted drug-resistant gliomas, enhancing permeation and inducing in tumor cells with reduced systemic toxicity. Other investigational efforts include antimicrobial hybrids combining borneol with (TCM) components, such as curcumin-loaded systems, which amplify photodynamic fungicidal effects against pathogens like through enhanced cellular uptake. Borneol-integrated hydrogels have also shown antibacterial and synergy in applications derived from TCM formulations. As of November 2025, no new borneol-based drugs from these emerging applications have received regulatory approval for clinical use.

References

  1. [1]
    Borneol | C10H18O | CID 64685 - PubChem - NIH
    Used to make perfumes. Borneol is a bornane monoterpenoid that is 1,7,7-trimethylbicyclo[2.2. 1]heptane substituted by a hydroxy group at position 2. It has a ...
  2. [2]
    Borneol - American Chemical Society
    Nov 20, 2023 · Borneol is a chiral bicyclic alcohol that exists in nature as two enantiomers, (–)- or L-borneol (shown) and (+)- or D-borneol.
  3. [3]
    Borneol | 507-70-0 - ChemicalBook
    Borneol has a piney, camphor-like odor and burning taste somewhat reminiscent of mint. Chemical Properties. Borneol is a bicyclic terpene alcohol. Borneol is an ...Missing: sources | Show results with:sources
  4. [4]
    The history, stereochemistry, ethnopharmacology and quality ...
    Jan 10, 2023 · Natural borneol​​ NB was originally derived from Dryobalanops aromatica, which is the genuine BO. However, due to the scarcity of resources, it ...
  5. [5]
    Borneol, Artemesia and Moxa - Institute for Traditional Medicine
    Synthetic borneol, obtained by simple chemical transformation of camphor and turpentine oil, is sometimes used in China as a substitute for the natural product.
  6. [6]
    Borneol, a novel agent that improves central nervous system drug ...
    Sources. Borneol's sources include natural extracts and artificial synthesis. One natural form of borneol is dextrorotatory borneol (endo-(1 R)-1,7,7-trimethyl ...Missing: history | Show results with:history
  7. [7]
    Borneol in cardio-cerebrovascular diseases - PubMed
    Apr 21, 2021 · This review summarizes the pharmacological actions and possible mechanisms of BO, which provides novel ideas for the treatment of CVDs.
  8. [8]
    Borneol: a Promising Monoterpenoid in Enhancing Drug Delivery ...
    Apr 28, 2021 · The current review focuses on the role of borneol as a permeation enhancer across the blood-brain barrier, mucosal barriers including nasal and ...
  9. [9]
    Bornane | C10H18 | CID 92108 - PubChem - NIH
    Bornane ; Molecular Formula. C10H ; Synonyms. Camphane; Bornane; Bornylane; 464-15-3; 1,7,7-Trimethylbicyclo[2.2.1]heptane ; Molecular Weight. 138.25 g/mol.
  10. [10]
    None
    ### Summary of Toxicity and Safety Information for Borneol (Sigma-Aldrich Product 68878)
  11. [11]
  12. [12]
    1H NMR Chemical Shift Changes as a Result of Introduction ... - MDPI
    Here, we report our complete assignments of the 1H NMR chemical shifts of borneol (1) and isoborneol (2), as well as their derivatives in which the hydroxy ...
  13. [13]
    Borneol (507-70-0) MS spectrum - ChemicalBook
    Borneol (507-70-0) MS Mass MS-NW-0600 borneol C10H18O (Mass of molecular ion: 154) Source Temperature: 260 °C Sample Temperature: 150 °C Reservoir, 75 eV
  14. [14]
    Purification of borneol from its isomeric mixture by using metal ...
    Jan 1, 2023 · Borneol and isoborneol are a pair of diastereomers with three chiral centers, and their high structural similarity leads to close physical ...Missing: stereoisomers | Show results with:stereoisomers
  15. [15]
    Conformations of borneol and isoborneol in the gas phase
    Nov 17, 2023 · Isomers and enantiomers of borneol, with the atom labeling used in this work and the chiral centers highlighted. The dashed red circles mark ...INTRODUCTION · Monomers · Water complexes · DMSO complexes
  16. [16]
    Investigation of borneols sold in Taiwan by chiral gas chromatography
    ... borneol. Chemically synthesized borneol contains four stereoisomers, (+)-isoborneol, (-)-isoborneol, (-)-borneol, and (+)-borneol. The ratio of these four ...
  17. [17]
    D-Borneol | C10H18O | CID 6552009 - PubChem - NIH
    Both D- and L- isomeric forms of borneol are naturally occurring(1). The most frequently encountered is L-borneol, characteristic of Compositae, Graminaceae and ...
  18. [18]
    Neutrophil Immunomodulatory Activity of (−)-Borneol, a Major ...
    We showed that essential oils isolated from G. squarrosa leaves and flowers potently inhibited intracellular Ca2+ mobilization [Ca2+]i in human neutrophils.
  19. [19]
    Borneol: A Plant-Sourced Terpene with a Variety of Promising ...
    Mar 2, 2022 · Background: Borneol, a bicyclic monoterpene belonging to the class of camphene, is sourced from Blumea balsamifera, Cinnamonum camphora (L.) ...<|control11|><|separator|>
  20. [20]
    Preparation of High-Purity (–)-Borneol and Xanthoxylin from Leaves ...
    To our knowledge, B. balsamifera has a relatively higher (–)-borneol content (about 1%) among them, which is also the only natural source for the preparation of ...
  21. [21]
    Use of Some Asteraceae Plants for the Treatment of Wounds - NIH
    Its leaves are rich in volatile compounds such as L-borneol (major compound), terpenoids, fatty acids, phenols, alcohols, aldehydes, ethers, ketones, pyridines, ...
  22. [22]
    Chemical profiling and biological assessment of essential oil from ...
    Aug 27, 2025 · The primary components included camphor (46.57%), endo-borneol (5.65%), eucalyptol (5.64%), and thymol (3.85%). The examination of herba-alba ...
  23. [23]
    Essential oil composition of Salvia rosmarinus Spenn. wild samples ...
    Among them, 1,8-cineole (26.4–49.1%), α-pinene (4.5–34.8%), camphor (1.1–18.8%) and borneol (1.7–16.2%) were the main constituents. The high amount of 1,8- ...
  24. [24]
    Compositon of the essential oil of rhizomes of kaempferia galanga L.
    pentadecane (9.0%), 1,8-cineole (5.7 %), 6-car-3- ene (3.3%) and borneol (2.7 %). Terpenoid constituents amounted to 16.4%. KEY WORDS. Kaempferia galanga L.
  25. [25]
    Unpredictable Chemical Diversity of Essential Oils in Cinnamomum ...
    Mar 8, 2024 · The earliest record for extracting natural D-borneol is from Dryobalanops aromatica C. F. Gaertn (Dipterocarpaceae) in Southeast Asia [19]. In ...
  26. [26]
    [PDF] Purity (–)-Borneol from Leaves of Blumea balsamifera (L) DC
    Natural (–)-borneol source is scarce in nature. Blumea balsamifera (L.) DC. is an important plant source for the extraction of natural (–)- borneol [11].
  27. [27]
    bornyl diphosphate synthase from Blumea balsamifera and its ...
    Borneol is a precious monoterpenoid with two chiral structures, (-)-borneol and (+)-borneol. Bornyl diphosphate synthase is the key enzyme in the borneol ...
  28. [28]
  29. [29]
  30. [30]
    Bornyl diphosphate synthase: Structure and strategy for carbocation ...
    Here, we report an x-ray crystal structure of a monoterpene cyclase, recombinant (+)-bornyl diphosphate synthase (BPPS) from Salvia officinalis (culinary sage) ...
  31. [31]
    Process for the preparation of borneol esters from turpentine.
    Paulst'rasse 8,) ave invented a new and use-' ful Improved Process forthe Preparation of Borneol and Isoborneol Esters from Oil of Turpentine, of-which the ...
  32. [32]
    Borneol - Foreverest Resources Ltd
    Synthetic Borneol is a high-performance product derived from alpha-pinene ... Consistent High Purity & Quality: The precise manufacturing process ...
  33. [33]
  34. [34]
    [PDF] Reduction of Camphor to Borneol using Sodium Borohydride
    Borneol is sterically hindered because for the reaction to occur the reducing agent would need to attack from the topside, but the dimethyl groups is hindering ...
  35. [35]
    [PDF] Camphor and its Industrial Synthesis
    The key point of isomerization synthesis is direct transformation of α-pinene (III) to camphene (V) which is also considered as a Wagner-Meervein rearrangement ...
  36. [36]
    Production of borneol, camphor, and bornyl acetate using ...
    Borneol, camphor, and bornyl acetate are naturally biosynthesized in the plants via the isoprenoid pathway, as follows (Fig. 1).
  37. [37]
    Green whole-cell biocatalysis: compartmentalized engineering of ...
    This whole-cell biocatalyst mediates the reduction of (+)-camphor to (+)-borneol under mild aqueous conditions (25 °C, pH 6.2) using isopropanol for NADPH ...
  38. [38]
    Mechanism of the chromic acid oxidation of secondary alcohols ...
    Mechanism of the chromic acid oxidation of secondary alcohols. Evidence which establishes the oxidative cleavage as a one-electron process. Click to copy ...
  39. [39]
    Engineering of a borneol dehydrogenase from P. putida for the ...
    Apr 12, 2021 · The natural sources for (-)-camphor are limited, and the oxidation of precious (-)-borneol would be too costly. Hence, synthesis of ...
  40. [40]
    Study on Synthesizing Isobornyl Acetate/Isoborneol from Camphene ...
    Feb 16, 2023 · This study examined the preparation of isobornyl acetate/isoborneol from camphene using an α-hydroxyl carboxylic acid (HCA) composite catalyst.
  41. [41]
    Bornyl acetate | 76-49-3 - ChemicalBook
    Oct 16, 2025 · Bornyl acetate is prepared by esterification of borneol with acetic anhydride or via the process described under borneol. Due to its ...
  42. [42]
    Bornyl acetate - American Chemical Society
    Dec 24, 2018 · Bornyl acetate's “piney” aroma makes it a common ingredient of perfumes used in air fresheners, cleaners, and personal care products.Missing: fragrances pharmaceuticals
  43. [43]
    Borneol - an overview | ScienceDirect Topics
    At the end of the last century, new resources were found to produce DB from Cinnamomum camphora in China, which provide the dominant production of natural DB in ...
  44. [44]
    Borneol (bing pian) - Herbs & Botanicals | Acupuncture Today
    In traditional Chinese medicine, borneol has an acrid, bitter taste and cool properties.It is associated with the Heart, Lung, Liver and Spleen meridians. How ...
  45. [45]
    Progress in Borneol Intervention for Ischemic Stroke - PubMed Central
    May 4, 2021 · Several proprietary Chinese medicine preparations such as Angong Niuhuang pills and Xingnaojing injection contain borneol and are widely ...
  46. [46]
    Unveiling the Medicinal Potentials of a Natural Bicyclic Compoun
    The natural sources of borneol include several aromatic plants and trees such as Blumea balsamifera, Dryobalanops aromatica, and Cinnamomum camphora. Borneol ...
  47. [47]
    Camphor in the Edo era - camphor and borneol for medicines
    Aug 7, 2025 · (+)-Borneol and its structural analogue camphor (Fig. 1) are used for analgesia and anaesthesia in traditional Chinese and Japanese medicine [13] ...Missing: Kampo | Show results with:Kampo
  48. [48]
    History of asthma | Asthma Control In Your Pocket - Smart Peak Flow
    Feb 8, 2025 · You can inhale incense, stuff it in a pipe, or roll up a cigar or cigarette. Turn of the century – belladonna, asthma cigarettes and injections.
  49. [49]
    laevo-borneol, 464-45-9 - The Good Scents Company
    Odor Type: balsamic. Odor Strength:medium , recommend smelling in a 10.00 % solution or less. Substantivity:16 hour(s) at 100.00 %. pine woody camphoreous ...
  50. [50]
    Borneol, (-)- | C10H18O | CID 1201518 - PubChem - NIH
    Constituents of lavandula dentata oil (including borneol) were identified by two GLS-MS systems. Muhtadi FJ et al; Spectrosc Lett 13 (7): 437 (1980). Hazardous ...
  51. [51]
    Fragrance material review on borneol - ScienceDirect.com
    Usage. Borneol is a fragrance ingredient used in decorative cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries as well as in non-cosmetic ...
  52. [52]
    Fragrance material review on borneol | Request PDF - ResearchGate
    Aug 7, 2025 · This compound is considered a GRAS (generally regarded as safe) approved by the FDA (US Food and Drug Administration) as food flavor [31] . ...
  53. [53]
    Repellent Effect of Borneols and Bornanediols against Aedes ...
    Feb 8, 2025 · Isoborneol and borneol are thought to have repellent activity against blood-sucking insects. However like many other natural compounds, their ...
  54. [54]
    US11246310B2 - Insect repelling composition - Google Patents
    A composition and method for insect repellent is provided. The composition in one form has on a weight percentage basis 2-4% α-pinene; 2-4% borneol; ...
  55. [55]
    Efficacy Tests of Commercial Skin-Applied Products in China - NIH
    Aug 28, 2022 · Apart from that, IR3535 was found to have synergistic effects when co-administered with DEET, and the combination of the two compounds could ...
  56. [56]
    Sanbexin® (Edaravone and Dexborneol Concentrated Solution for ...
    Jul 30, 2020 · Sanbexin® (Edaravone and Dexborneol Concentrated Solution for Injection) was Approved by NMPA on the Chinese Market · On July 30, 2020, the ...
  57. [57]
    China NMPA approves Simcere's Sanbexin® sublingual tablets for ...
    Dec 4, 2024 · Previously, Sanbexin® injection was approved for marketing in China in 2020. As the world's only innovative drug approved for stroke since 2015, ...
  58. [58]
    Borneol influences the pharmacokinetics of florfenicol ... - PubMed
    Aug 26, 2021 · Borneol is a traditional Chinese medicine. In Chinese veterinary clinics, borneol and its related compounds are often used in combination ...
  59. [59]
  60. [60]
    The Role and Mechanism of Borneol to Open the Blood-Brain Barrier
    Apr 13, 2018 · Recent studies showed that borneol could promote penetration of methotrexate, nimustine, and other drugs through the BBB, increasing drug ...
  61. [61]
    Borneol's Influence on Blood-Brain Barrier Permeability and ... - Nature
    By altering cell junctions and downregulating efflux transporters, borneol facilitates greater penetration of drugs into targeted brain regions. These ...
  62. [62]
    Role of borneol as enhancer in drug formulation: A review
    As a traditional Chinese medicine (TCM), borneol has shown superior ability for anti-inflammatory and analgesic activities when coupled with other active ...
  63. [63]
    Borneol, a novel agent that improves central nervous system drug ...
    The BBB-opening effect of borneol is a reversible physiological process characterized by rapid and transient penetration of the BBB and highly specific brain ...
  64. [64]
    Analgesic and anti-inflammatory effects and mechanism of action of ...
    Borneol has significant analgesic and anti-inflammatory effects on PDT of acne, and enhances the healing of acne by activating p38-COX-2-PGE2 signaling pathway.
  65. [65]
    Borneol's Pre-Clinical Analgesic Efficacy: Mediated by Receptor and ...
    Aug 13, 2025 · Borneol is frequently utilized as an adjunct component in traditional Chinese medicine for the treatment of cardiovascular and cerebrovascular ...
  66. [66]
    Dexborneol Amplifies Pregabalin's Analgesic Effect in Mouse ...
    Jul 2, 2024 · Dexborneol facilitates pregabalin's CNS penetration, disrupting self-amplifying inflammatory and oxidative cycles by inhibiting the TLR4/NF-κB ...
  67. [67]
    Effects of Natural Borneol on Germ Tube Formation and Preformed ...
    Sep 29, 2022 · Our study also found that borneol inhibited between 33.7% and 58.2% of the preformed biofilm activity at concentrations between 0.25 and 4 mg/mL ...
  68. [68]
    Antibiofilm Activities of Borneol-Citral-Loaded Pickering Emulsions ...
    Oct 4, 2022 · Borneol alone was able to reduce the number of viable bacteria by 1.3 log units at a concentration of 2.5 mg/mL (Fig. S1), while at the same ...
  69. [69]
    (+)-Borneol is neuroprotective against permanent cerebral ischemia ...
    Here, we report that in the rat model of permanent cerebral ischemia, we found that (+)-borneol (1.0 mg/kg) significantly ameliorated infarct size and ...
  70. [70]
    Progress in Borneol Intervention for Ischemic Stroke - Frontiers
    May 3, 2021 · Borneol is effective in the prevention and treatment of nerve injury in ischemic stroke. Its mechanisms of action include improvement of cerebral blood flow.
  71. [71]
    Chemoinformatics investigation of newly designed borneol and ...
    Chemoinformatics investigation of newly designed borneol and phenolic diterpenoid derivatives as potential anti-influenza A virus agents.
  72. [72]
    Edaravone Dexborneol Versus Edaravone Alone for the Treatment ...
    Feb 16, 2021 · The TASTE trial (Treatment of Acute Ischemic Stroke with Edaravone Dexborneol) was a phase III, randomized, double-blind, parallel ...
  73. [73]
    (+)-Borneol inhibits the generation of reactive oxygen species and ...
    Nov 7, 2022 · (+)-Borneol decreases the ROS level in activated neutrophils and inhibits NETosis triggered by PMA stimulation in vitro.
  74. [74]
    Protection by borneol on cortical neurons against oxygen-glucose ...
    We demonstrated that borneol reversed OGD/R-induced neuronal injury, nuclear condensation, intracellular reactive oxygen species (ROS) generation, and ...
  75. [75]
    [PDF] Borneol - NJ.gov
    Borneol can cause eye/skin irritation, nose/throat irritation, headache, nausea, vomiting, dizziness, and may cause skin allergy. No exposure limits are set.Missing: maximum | Show results with:maximum
  76. [76]
    (+)- And (-)-borneol: efficacious positive modulators of GABA action ...
    Apr 1, 2005 · (+)-Borneol was found to have a highly efficacious positive modulating action at GABA(A) receptors, as did its enantiomer (-)-borneol.Missing: headache nausea seizures
  77. [77]
    [PDF] Update to RIFM fragrance ingredient safety assessment, borneol ...
    Apr 15, 2022 · The exposure level for borneol is below the Cramer Class I TTC value for inhalation exposure local effects. 11.1.6.1. Risk assessment. There ...
  78. [78]
    Substances Added to Food (formerly EAFUS)
    FEMA has established expert panels to evaluate and make independent determinations on the GRAS status of flavoring substances.
  79. [79]
    [PDF] OPINION on Fragrance allergens in cosmetic products
    1 Human hygiene biocidal products. 2 Private area and public health area disinfectants and other biocidal products. 3 Veterinary hygiene biocidal products. 10 ...
  80. [80]
    Edaravone Dexborneol in acute ischemic stroke patients treated ...
    Oct 21, 2025 · Patients treated with Edaravone Dexborneol were associated with better functional outcomes three months after stroke onset compared to those who ...
  81. [81]
    Synthesis and in vitro study of novel borneol derivatives as potent ...
    Herein, we present the design and synthesis of a series of novel heterocyclic derivatives of (–)-borneol and (–)-isoborneol as potent inhibitors of the ...
  82. [82]
  83. [83]
    Buy Bornyl chloride, (+)- | 30462-53-4 - Smolecule
    Rating 5.0 (6) Its molecular formula is C₁₀H₁₇Cl, and it has a molecular weight of approximately 172.69 g/mol. Bornyl chloride is classified as a saturated terpene and is ...
  84. [84]
    X. Jones Reaction: The Oxidation of Borneol to Camphor
    A very important group of oxidation reactions uses various forms of chromium as the oxidizing agent. Reactions of this type are called Jones oxidations.
  85. [85]
    [PDF] EXP. 35 A OXIDATION OF BORNEOL TO CAMPHOR C R H H R C ...
    Experiment 35 involves oxidizing borneol to camphor using sodium hypochlorite, then reducing it back to isoborneol with sodium borohydride.
  86. [86]
    Showing Compound Bornyl isovalerate (FDB017540) - FooDB
    Bornyl isovalerate belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are ...Missing: nitroborneol | Show results with:nitroborneol
  87. [87]
    Design, synthesis and evaluation of NBP/borneol hybrids as ...
    Design, synthesis and evaluation of NBP/borneol hybrids as neuroprotective agents for the treatment of ischemic stroke. September 2025; Bioorganic Chemistry ...Missing: conjugate | Show results with:conjugate
  88. [88]
    Traditional Chinese Medicine Borneol‐Based Polymeric Micelles ...
    Jan 13, 2025 · ... dosage have not yet been thoroughly identified. Borneol is typically administered orally in oil or capsules at high dosages (>200 mg·kg−1 ...
  89. [89]
    Synthesis and Biological Activity of Borneol Esters - ResearchGate
    Aug 10, 2025 · Borneol derivatives have been regarded as promising anti-inflammatory and antimicrobial agents. In this work, eight borneol esters (1-8) ...Missing: fragrances pharmaceuticals
  90. [90]
    Borneol serves as an adjuvant agent to promote the cellular uptake ...
    In this study, we showed that borneol improved the cellular uptake of curcumin, thereby enhancing its photodynamic fungicidal efficacy against C. albicans.
  91. [91]
    Advances and Challenges in Nano-Delivery Systems for ...
    Aug 4, 2025 · FDA has approved multiple chemotherapeutic agents for brain tumor treatment. Among these, TMZ is the first-line chemotherapeutic agent for GBM.
  92. [92]
    Borneol-modified docetaxel plus tetrandrine micelles for treatment of ...
    Borneol (BO) modified in micelles has been shown to promote DTX plus TET to cross the BBB, allowing the drug to better act on tumors.
  93. [93]
    Multiple crosslinked, self-healing, and shape-adaptable hydrogel ...
    Borneol, a traditional Chinese medicine, features cooling, pain-easing, antibacterial, and anti-inflammatory properties and has been used as a drug additive ...