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Citronellal

Citronellal is a naturally occurring monoterpenoid aldehyde with the molecular formula C₁₀H₁₈O and the IUPAC name 3,7-dimethyloct-6-enal, characterized by its colorless to pale yellow liquid form and a strong, fresh lemon-citronella odor.^[1] It exists as optical isomers, primarily the (+)- and (-)-enantiomers, and has a molecular weight of 154.25 g/mol, with physical properties including a boiling point of 205–207 °C and a density of 0.850–0.860 g/cm³ at 20 °C.^[1] As a key component in essential oils from plants like Cymbopogon nardus, C. winterianus, C. citratus, and Eucalyptus citriodora, citronellal is obtained through fractional distillation or extraction methods such as hydrodistillation.^[2]^[1] In industrial applications, citronellal serves as a vital fragrance ingredient in perfumes, cosmetics, soaps, and detergents, imparting citrus and fresh notes, and is also employed as a flavoring agent in food products.^[1] It functions as an intermediate in organic synthesis, notably in the production of (-)-menthol via processes like the Takasago asymmetric synthesis, where it undergoes hydrogenation and cyclization.^[2] Additionally, citronellal exhibits insect-repellent properties, particularly against mosquitoes, and is incorporated into repellents derived from citronella oil.^[1] Citronellal demonstrates a range of biological activities, including antibacterial effects against pathogens such as Staphylococcus aureus and Escherichia coli (with minimum inhibitory concentrations typically in the range of 0.5–2 mg/mL), antifungal activity against Candida species, and insecticidal efficacy against pests like Tribolium castaneum and Sitophilus spp.^[2] It also shows anti-inflammatory, antioxidant, antiviral, and antinociceptive properties in various studies.^[2] Regarding safety, citronellal is moderately irritating to skin and eyes, with potential for allergic contact dermatitis, though oral and dermal LD50 values in rats and rabbits exceed 2.5–5 g/kg, indicating low acute toxicity; it is classified as harmful to aquatic life with long-lasting effects under GHS guidelines.^[1]

Chemical Identity

Nomenclature and Structure

Citronellal is an organic compound classified as a monoterpenoid aldehyde, with the molecular formula \ce{C10H18O} and a molecular weight of 154.25 g/mol.^[1] Its systematic IUPAC name is 3,7-dimethyloct-6-enal, reflecting the eight-carbon chain with an aldehyde functional group at carbon 1, a terminal double bond between carbons 6 and 7, and methyl substituents attached to carbons 3 and 7.^[1] As an acyclic monoterpenoid, citronellal features a linear hydrocarbon backbone interrupted by the specified methyl branches and unsaturation, which contribute to its role as a key volatile in natural product chemistry.^[1] The molecule contains a chiral center at carbon 3, giving rise to a pair of enantiomers: the (3R)-(+)-citronellal and the (3S)-(−)-citronellal.^[1] In natural isolates, the (3S)-(−)-enantiomer predominates, often achieving enantiomeric excesses (ee) of up to 80% in essential oils from sources such as Backhousia citriodora.^[1] The optically pure (3S)-(−)-enantiomer displays a specific rotation of [\alpha]^{20}_D = -15^\circ (neat).^[3] The two-dimensional structure of citronellal is typically depicted as a straight-chain aldehyde with the formula \ce{HC(=O)CH2CH(CH3)CH2CH2CH=C(CH3)CH3}, highlighting the aldehyde terminus, the branched methyl at the chiral C3, and the 1-methylethenyl (isopropenyl) group at the opposite end.^[1] In three-dimensional representations, the molecule adopts a flexible, extended conformation due to its aliphatic nature, with the chiral center at C3 influencing the spatial arrangement of the side chain; computational models often show a zig-zag backbone with the double bond in the E configuration, though the natural isolate may exhibit conformational variability.^[1]

Physical and Chemical Properties

Citronellal is a colorless to pale yellow liquid at room temperature, characterized by a strong lemon-like odor with green and rose notes.^[1]^[4] Its density is 0.857 g/cm³ at 25 °C, with a boiling point ranging from 201 to 207 °C at standard pressure.^[5]^[6] The refractive index is approximately 1.451 at 20 °C.^[5] Citronellal exhibits low solubility in water (approximately 0.04 g/L at 25 °C), but is soluble in ethanol and ether.^[1]^[7] The compound is air-sensitive and susceptible to oxidation by atmospheric agents, such as hydroxyl radicals, as well as polymerization, particularly under acidic or basic conditions; it remains stable under neutral storage conditions below 30 °C.^[6]^[8] Citronellal's aldehyde group enables typical reactions including oxidation to the corresponding carboxylic acid (citronellic acid), reduction to the primary alcohol (citronellol), and participation in aldol condensations.^[1] The isolated double bond in its structure allows for hydrogenation to form dihydrocitronellal or epoxidation to yield the epoxide derivative.^[1] These reactive sites contribute to its utility in organic synthesis, stemming from its molecular formula C₁₀H₁₈O.^[1]

Natural Occurrence

Plant Sources

Citronellal is primarily obtained from the essential oils of grasses in the genus Cymbopogon, particularly Cymbopogon nardus (Ceylon citronella) and Cymbopogon winterianus (Java citronella), where it constitutes a major component of the oil. In C. nardus essential oil, citronellal typically ranges from 5% to 15% of the total composition, with reported values up to 22% depending on cultivation conditions.^[9] In C. winterianus oil, citronellal content varies from 30% to 45%, such as 32.61%, 33.06%, and up to 38.82% in analyzed samples from Indian and Indonesian sources.^[10]^[11] These plants yield essential oil at rates of 1.0% to 1.5% on a dry weight basis, with C. winterianus often producing higher overall volumes compared to C. nardus.^[12] Other notable plant sources include the lemon-scented gum (Corymbia citriodora), native to Australia, whose leaf oil contains citronellal at elevated levels of 65% to 85%, with specific analyses showing 76.3% to 83.2%. Kaffir lime (Citrus hystrix), a citrus species from tropical Southeast Asia, has citronellal as the dominant compound in its leaf oil, comprising 46% to 85%, including 77.29% and 84.2% in regional variants. Various other Citrus species also contribute smaller amounts of citronellal to their essential oils, though less prominently than in C. hystrix. These plants are predominantly distributed in tropical regions, with Cymbopogon nardus originating from Sri Lanka and India and cultivated across Southeast Asia, while C. winterianus is widely grown in India and Indonesia. Corymbia citriodora is endemic to eastern Australia, and Citrus hystrix thrives in Southeast Asian countries like Thailand and Indonesia. Natural extracts of citronellal exhibit enantiomeric predominance, with Cymbopogon species yielding mostly the (R)-(+)-enantiomer at enantiomeric excesses (ee) of around 88%, whereas kaffir lime oils favor the (S)-(−)-enantiomer up to 80% ee. Citronellal was first isolated from citronella oil in the late 19th century, with the term entering scientific literature around 1890.

Biosynthesis in Plants

Citronellal, an acyclic monoterpenoid aldehyde, is biosynthesized in plants primarily through the 2-C-methyl-D-erythritol-4-phosphate (MEP) pathway localized in plastids, which generates the isoprenoid precursors isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). These units condense to form geranyl diphosphate (GPP), the universal C10 precursor for monoterpenes, via the action of geranyl diphosphate synthase. In species like Cymbopogon winterianus and Cymbopogon nardus, isotope labeling studies using [14C]-mevalonate and [3H]-labeled precursors have confirmed that GPP is transformed into geraniol intermediates, leading to citronellal production.^[13]^[14] The process exhibits high enantioselectivity, with plants predominantly producing the (R)-(+)-enantiomer of citronellal. Enantioselective gas chromatography analyses of essential oils from Cymbopogon species reveal enantiomeric excesses up to 88% for (R)-citronellal, underscoring the stereospecificity of these enzymatic transformations. This chirality is crucial for the compound's biological activity and integration into plant volatile profiles.^[15]^[16] Biosynthesis of citronellal is tightly regulated by environmental cues, particularly in Cymbopogon species where light intensity and abiotic stresses modulate enzyme expression and flux through the MEP pathway. Full sunlight exposure induces oxidative stress, elevating reactive oxygen species that upregulate terpenoid production as a protective response, while shade reduces overall yields but alters composition toward higher citronellal proportions. Drought and salinity stresses similarly enhance MEP pathway genes, such as 1-deoxy-D-xylulose-5-phosphate synthase, leading to increased citronellal accumulation during peak seasonal periods like October-November in subtropical regions.^[14]^[17]^[18] Evolutionarily, citronellal biosynthesis represents an adaptation within the broader terpenoid system, serving dual roles in plant defense against herbivores and pathogens via repellency and toxicity, as well as in attracting pollinators and beneficial insects through volatile signaling. Phylogenetic analyses indicate that such monoterpenoid pathways diversified in angiosperms to enhance ecological interactions, with lineage-specific enzymes evolving to optimize these functions in aromatic grasses like Cymbopogon.^[19]^[20]

Production

Extraction Methods

The primary method for extracting citronellal from natural sources involves steam distillation of leaves from citronella grass, particularly Cymbopogon nardus, which contains high concentrations of the compound in its essential oil.^[1] In this process, fresh or partially dried leaves are subjected to steam, which volatilizes the oil components; the vapor is then condensed and separated, yielding typically 0.5-1.5% essential oil by weight of the plant material. The resulting citronella oil from Java-type varieties (Cymbopogon winterianus) contains 32-45% citronellal, while Ceylon-type (C. nardus) oils have lower levels of 5-15%.^[10]^[21] To isolate and purify citronellal from the crude oil, fractionation techniques such as vacuum distillation are employed, which lower the boiling points to prevent thermal degradation of terpenoids.^[22] This batch vacuum fractional distillation separates citronellal (boiling point around 205-208°C at atmospheric pressure, reduced under vacuum) from co-occurring compounds like geraniol and citronellol, achieving purities up to 75-80% in distillate fractions.^[23] Molecular distillation offers an alternative for higher purity, using short-path evaporation under high vacuum to further refine the fraction by minimizing residence time and avoiding decomposition.^[24] Solvent extraction serves as a supplementary method for oil recovery, particularly when steam distillation yields are suboptimal, using non-polar solvents like hexane or polar ones like ethanol to dissolve and extract the oil from macerated leaves.^[25] The solvent is then evaporated, and the crude extract undergoes rectification—fractional distillation under reduced pressure—to concentrate citronellal while removing solvent residues and impurities.^[26] This approach can enhance recovery in solvent-assisted variants like microwave-assisted extraction, though it requires careful solvent recovery to maintain oil quality. Yield factors significantly influence extraction efficiency, with optimal harvesting occurring just before or at the flowering stage, when oil content peaks due to accumulated terpenoids in the leaves.^[27] Regional variations also play a role; Java-origin plants (C. winterianus) generally provide higher citronellal yields (up to 1.2% oil with 35% citronellal) compared to Ceylon varieties, attributed to climatic and varietal differences in tropical cultivation areas.^[28]^[29] Historical methods for citronella oil extraction emerged in the early 20th century alongside the growth of the essential oil industry in Southeast Asia and Central America, where steam distillation became standardized for commercial production from introduced citronella grasses.^[30] Early developments focused on improving distillation apparatus to boost yields from 0.5% to over 1%, driven by rising demand for natural insect repellents and fragrances.^[31]

Synthetic Routes

The primary industrial method for producing citronellal involves the selective hydrogenation of citral, a mixture of neral and geranial, using supported metal catalysts such as palladium on carbon or nickel-based systems.^[32] This process targets the conjugated double bond in citral while preserving the isolated one, typically conducted under mild conditions of 50–100 °C and 1–5 bar hydrogen pressure in solvents like methanol or ethanol, often with additives like triethylamine to enhance selectivity.^[33] Industrial yields exceed 90%, making this route highly scalable and economical for large-scale production.^[32] Alternative chemical routes include the asymmetric isomerization of geranyldiethylamine, derived from myrcene, using rhodium complexes with chiral diphosphine ligands such as (S)-BINAP to yield enantiopure (R)-citronellal after hydrolysis of the intermediate enamine.^[34] This method, pioneered by Takasago International, achieves high enantiomeric excess (>95% ee) and is employed industrially for chiral citronellal, serving as a key step in (-)-menthol synthesis.^[35] Citronellal produced via these routes is commonly used as an intermediate for menthol, involving acid-catalyzed cyclization to isopulegol followed by hydrogenation.^[36] Biotechnological alternatives utilize enzymatic cascades, such as the oxidation of geraniol to citral using copper radical alcohol oxidases, followed by stereoselective reduction with old yellow enzymes (OYEs) to produce (R)- or (S)-citronellal.^[37] These bienzymatic systems, often implemented in whole-cell Escherichia coli hosts, offer sustainable production with high enantioselectivity (up to 99% ee) and atom efficiency, bypassing the need for chemical reductants.^[38] Recent advances in bio-production include engineered E. coli strains expressing bienzymatic cascades from geraniol, achieving yields of up to 95% ee and gram-scale titers in 2025 studies, enhancing scalability for chiral variants.^[38] These developments prioritize green chemistry principles, with cofactor recycling via glucose dehydrogenase to maintain process efficiency.^[37]

Applications

Fragrance and Flavor Uses

Citronellal serves as a key ingredient in perfumery, where it functions as a top note imparting fresh, green-lemon aromas with citrusy, fruity-floral, and herbaceous undertones, particularly in citrus, floral, and woody fragrance compositions.^[39] It provides a sharp, bright lift that enhances lemongrass and lemon accords, often used at concentrations of 0.5-10% in fragrance concentrates to achieve authentic citrus character or to modify other notes.^[40] With moderate tenacity, citronellal evaporates over 2-4 hours on a smelling strip, offering a volatile diffusion peak within 15-30 minutes, which requires pairing with fixatives like rose alcohols or musks to extend longevity in formulations.^[41] In cosmetics and soaps, citronellal is incorporated in small amounts, typically 0.1-1%, to impart scent in products such as detergents, shampoos, and toiletries, where its fresh profile contributes to overall cleanliness and appeal.^[1] Synthetic versions are preferred over natural isolates for their consistent purity and odor quality, avoiding variations from plant sources like citronella oil.^[41] For flavoring applications, citronellal holds Generally Recognized as Safe (GRAS) status from the FDA and FEMA, allowing its use in small quantities up to 10 ppm in beverages, candies, and non-alcoholic drinks to deliver a rosy-citrus taste with leafy and fatty nuances.^[42] Specific levels include 1.31-5.04 ppm in alcoholic beverages and 6.07-7.96 ppm in baked goods, enhancing citrus and herbal profiles without overpowering other ingredients.^[1] Historically, citronellal entered synthetic perfumery in the 1920s as a commercial alternative to natural citronella oil, enabling reproducible lemon-like scents in modern fragrance development.^[41] Global annual production reaches approximately 2,000 tons of synthetic (R)-citronellal, primarily destined for the fragrance industry, supplemented by extraction from 2,300 tons of citronella oil yielding 40-50% citronellal content.^[43]

Biological and Pharmaceutical Applications

Citronellal exhibits notable antimicrobial properties, particularly against fungal and bacterial pathogens. It demonstrates antifungal activity against Candida species, with minimum inhibitory concentrations (MICs) as low as 0.06% v/v against C. valida, effectively inhibiting growth by disrupting membrane integrity.^[44] In bacterial contexts, citronellal shows moderate efficacy against both Gram-positive and Gram-negative strains, such as Staphylococcus aureus (MIC 400 μg/mL) and Escherichia coli, through mechanisms including membrane disruption.^[45] These effects position citronellal as a promising natural agent for combating microbial infections, especially in essential oil-based formulations. As of 2025, citronellal has been incorporated into chitosan coatings for titanium surfaces, enhancing antibacterial activity against S. aureus and E. coli in biomedical applications.^[46] As an antioxidant, citronellal scavenges free radicals, with an IC50 of 79.90 μg/mL (approximately 520 μM) in DPPH assays.^[47] Its anti-inflammatory effects have been demonstrated in rat models of paw edema, reducing carrageenan-induced inflammation by 18.5-22.3% and arachidonic acid-induced edema by 31-38.8% at doses of 100-200 mg/kg, potentially through inhibition of reactive oxygen species.^[48] Citronellal also displays insect-repellent properties, particularly against mosquitoes, and insecticidal efficacy against pests such as Tribolium castaneum (red flour beetle) and Sitophilus spp. (weevils), with LC50 values reported in the range of 0.5-2% in fumigation studies.^[1] Beyond these roles, citronellal shows anthelmintic activity against gastrointestinal nematodes in sheep, reducing parasite burden via disruption of parasite membranes and motility.^[49] Preliminary anticancer research indicates it induces apoptosis in cancer cell lines, such as MDA-MB-231 triple-negative breast cancer cells, by upregulating pro-apoptotic Bax, downregulating anti-apoptotic Bcl-2, and activating caspase-3, with IC50 values as low as 1.41 nM.^[50] These findings, from studies up to 2024, suggest exploratory therapeutic potential, though further clinical validation is needed.^[51] In pharmaceutical applications, citronellal serves as a key intermediate in the synthesis of menthol, undergoing cyclization to isopulegol followed by hydrogenation, enabling efficient one-pot production over catalysts like Ni-supported zeolites.^[52] It is also incorporated into essential oil formulations for topical antifungals, enhancing efficacy against Candida biofilms when combined with carriers like Cymbopogon nardus extracts.^[53] The bioactive mechanisms of citronellal stem from its aldehyde group, which interacts with microbial enzymes and disrupts metabolic pathways, while its terpenoid backbone increases membrane permeability, facilitating entry and depolarization in target cells.^[54] These structural features underpin its broad biological applications without overlapping into sensory or toxicological domains.

Safety and Regulation

Toxicology Profile

Citronellal exhibits low acute toxicity via oral and dermal routes. The oral LD50 in rats exceeds 5,000 mg/kg, indicating minimal risk from ingestion in single exposures.^[1] Similarly, the dermal LD50 in rabbits is greater than 2,500 mg/kg, suggesting low systemic absorption through the skin under acute conditions.^[1] As a skin irritant classified under GHS Skin Irritation Category 2 (H315), citronellal causes moderate irritation upon direct contact with rabbit skin in occluded tests.^[1] It is also a potential skin sensitizer (GHS Skin Sensitization Category 1B, H317), capable of inducing allergic contact dermatitis in sensitive individuals, though human patch tests at 4% concentration showed no sensitization in 25 volunteers.^[1] Eye exposure results in serious irritation (GHS Eye Irritation Category 2, H319).^[1] Chronic exposure studies reveal no evidence of carcinogenicity, with citronellal not classified as a carcinogen by relevant agencies.^[55] Standard reproductive toxicity tests, including developmental assessments, show no adverse effects, and it is not classified as a reproductive toxicant.^[56] Citronellal is toxic to aquatic organisms, classified under GHS Aquatic Chronic Hazard Category 2 (H411), with long-lasting effects. The 96-hour LC50 for fish (Leuciscus idus) is approximately 22 mg/L, highlighting risks to aquatic ecosystems from environmental release.^[57] In occupational settings, primary exposure routes are dermal contact and inhalation during handling, with incidental ingestion possible but less common.^[1] Upon absorption, citronellal undergoes metabolism primarily to citronellic acid via oxidation, along with minor pathways leading to conjugated metabolites that are excreted in urine.^[1]

Regulatory Status

Citronellal is recognized as generally recognized as safe (GRAS) by the U.S. Food and Drug Administration (FDA) for use as a synthetic flavoring substance and adjuvant in food under 21 CFR 172.515, provided it is used in the minimum quantity required to produce its intended effect in accordance with good manufacturing practices.^[58] In the European Union, it is approved for use as a flavoring substance in foodstuffs under Regulation (EC) No 1334/2008, as amended, following safety evaluations by the European Food Safety Authority (EFSA). For cosmetic applications, the International Fragrance Association (IFRA) sets usage restrictions on citronellal in fragrance ingredients to mitigate risks of skin sensitization, with maximum permitted levels varying by product category—for instance, up to 0.41% in lip products (Category 1) and lower concentrations such as 0.026% in certain body lotions (Category 3) under Amendment 49 to the IFRA Standards.^[59] In the European Union, citronellal is not subject to specific quantitative restrictions under Annex III of the Cosmetics Regulation (EC) No 1223/2009 but must be labeled if present above 0.001% in leave-on products or 0.01% in rinse-off products as a potential fragrance allergen.^[60] Regarding pesticide use, the U.S. Environmental Protection Agency (EPA) exempts oil of citronella—a primary natural source of citronellal—from federal tolerance requirements for residues on food commodities when applied as a biochemical pesticide in insect repellents, based on a 1996 ruling under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA).^[61] This exemption reflects the low toxicity profile of citronella oil components, supporting their classification as minimum-risk pesticides. Citronellal itself is addressed within standards for essential oils in the United States Pharmacopeia (USP)/National Formulary (NF), particularly for purity specifications in fragrance-related grades.^[62] Internationally, citronellal (CAS 106-23-0) is registered under the European Union's REACH Regulation (EC) No 1907/2006, ensuring compliance with chemical safety assessments for manufacture and import above one tonne per year.^[63]

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A Review on Anti-Inflammatory Activity of Monoterpenes - PMC
These findings support the popular use of geraniol and citronellol as anti-inflammatory agents, thus suggesting a therapeutic potential for inflammation- ...Missing: IC50 | Show results with:IC50
[45]
Research progress on chemical composition, biological activity and ...
Furthermore, citral exhibits antioxidant and anti-inflammatory properties, which may reduce the generation of reactive oxygen species (ROS) and the release of ...
[46]
[PDF] Anthelmintic activity of Eucalyptus citriodora essential oil and its ...
This study aimed to evaluate the anthelmintic activity of Eucalyptus citriodora essential oil and citronellal on sheep gastrointestinal nematodes.<|control11|><|separator|>
[47]
Anticancer Effect of Citrus hystrix DC. Leaf Extract and Its Bioactive Constituents Citronellol and, Citronellal on the Triple Negative Breast Cancer MDA-MB-231 Cell Line
### Summary of Citronellal's Anticancer Effects
[48]
Citronellal suppress the activity of ornithine decarboxylase in ...
The anticancer potential of citronellal has not been explored in detail, and no report has been found so far against FaDu cell line. Since cell proliferation ...Citronellal Suppress The... · 3. Results · 3.2. Citronellal Inhibits...
[49]
One-Pot Synthesis of Menthol Starting from Citral over Ni Supported ...
Aug 25, 2022 · The most promising catalyst in the one-pot menthol synthesis was Ni supported first on H-Beta-38 and then extruded with attapulgite giving a 45% yield of ...
[50]
The antifungal and antibiofilm activity of Cymbopogon nardus ... - NIH
C. nardus EO and citronellal effectively inhibited biofilm formation (p < 0.05) and disrupted preformed biofilms (p < 0.0001). They most likely interact with ...
[51]
Antibiofilm activity of the essential oil of citronella (Cymbopogon ...
Monoterpenes have the ability to cross the cell wall and the ability to permeabilize and depolarize the plasma membrane (Tong et al., 2013).
[52]
Citronellal - Registration Dossier - ECHA
Toxicity to reproduction. Endpoint summary ... For the derivation of systemic long term DNELs, no repeated dose toxicity studies available for citronellal.
[53]
https://pmc.ncbi.nlm.nih.gov/articles/PMC9433487/
[54]
[PDF] Citronellal - Safety data sheet - BASF
Sep 7, 2023 · Assessment of aquatic toxicity: Acutely toxic for aquatic organisms. ... Toxicity to fish: LC50 (96 h) approx. 22 mg/l, Leuciscus idus (DIN ...
[55]
21 CFR 172.515 -- Synthetic flavoring substances and adjuvants.
Synthetic flavoring substances and adjuvants may be safely used in food in accordance with the following conditions.Missing: GRAS | Show results with:GRAS
[56]
[PDF] Amendment 49 STAND Citronellal IFRA STANDARD RESTRICTION
Feb 10, 2021 · It should further be noted that natural complex substances themselves can be restricted by an IFRA Standard. For a detailed list of natural ...
[57]
Regulation (EC) No 1223/2009 of the European Parliament and of ...
List of substances which cosmetic products must not contain except subject to the restrictions laid down.
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Reregistration Eligibility Decision (RED) Fact Sheet for Oil of Citronella
On February 28, 1996, the Agency issued a rule exempting certain pesticides, including oil of citronella, from regulation under FIFRA.Missing: 2004 | Show results with:2004
[59]
USP-NF
USP–NF is a combination of two compendia, the United States Pharmacopeia (USP) and the National Formulary (NF).Purchase USP–NF · USP-NF Standard Updates · New USP-NF Publication ModelMissing: citronellal | Show results with:citronellal
[60]
https://www.legislation.gov.uk/eur/2009/1223/annex/III