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Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Appearance: | white powder (est) |
| Assay: | 98.00 to 100.00 %
|
| Food Chemicals Codex Listed: | No |
| Specific Gravity: | 0.94300 @ 25.00 °C.
|
| Refractive Index: | 1.46500 @ 20.00 °C.
|
| Melting Point: | 37.00 to 39.00 °C. @ 760.00 mm Hg
|
| Boiling Point: | 202.00 to 203.00 °C. @ 760.00 mm Hg
|
| Vapor Pressure: | 0.069000 mmHg @ 25.00 °C. (est) |
| Vapor Density: | 5.3 ( Air = 1 ) |
| Flash Point: | 167.00 °F. TCC ( 75.00 °C. )
|
| logP (o/w): | 2.550 (est) |
| Soluble in: |
| | alcohol | | | water, 461.4 mg/L @ 25 °C (est) |
Organoleptic Properties:
| |
| Odor Type: earthy |
| |
| Odor Strength: | medium |
| |
| Substantivity: | 12 hour(s) at 100.00 % |
| |
| | earthy woody |
Odor Description: at 100.00 %. | earthy woody |
| |
| | clean cooling camphoreous pine woody eucalyptus green herbal minty |
Odor Description: at 1.00 %. | Clean cooling camphoraceous, piney with a woody eucalyptol and slight green herbal minty nuances Mosciano, Gerard P&F 25, No. 6, 26, (2000) |
| |
| |
| Flavor Type: camphoreous |
| |
| | camphoreous cooling pine earthy minty citrus lime spicy |
Taste Description: at 1.00 - 5.00 ppm. | Intense camphoraceous, cooling, piney with an earthy nuance. It has minty-citrus lime and spicy notes Mosciano, Gerard P&F 25, No. 6, 26, (2000) |
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
| European information : |
| Most important hazard(s): | | Xi - Irritant |
R 38 - Irritating to skin. S 02 - Keep out of the reach of children. S 24 - Avoid contact with skin. S 36 - Wear suitable protective clothing.
|
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
|
Not determined
|
| Dermal Toxicity: |
|
Not determined
|
| Inhalation Toxicity: |
|
Not determined
|
Safety in Use Information:
| Category: | flavor and fragrance agents |
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice |
| Recommendation for (-)-alpha-fenchol usage levels up to: | | | 8.0000 % in the fragrance concentrate.
|
| |
| Recommendation for (-)-alpha-fenchol flavor usage levels up to: |
| | 5.0000 ppm in the finished product.
|
Safety References:
| Flavor & Extract Manufacturers Association (FEMA) reference(s): |
| The FEMA GRAS assessment of alicyclic substances used as flavor ingredients. View pdf |
| EPI System: | View |
| EPA Substance Registry Services (TSCA): | 512-13-0 |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 439711 |
| National Institute of Allergy and Infectious Diseases: | Data |
| | (1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol |
| Chemidplus: | 0000512130 |
References:
Other Information:
Potential Blenders and core components note
| |
| For Odor |
| No odor group found for these |
| | tagete oil rwanda | |
| amber |
| sports | amber fragrance | FR |
| anisic |
| | estragole | FL/FR |
| balsamic |
| laevo- | borneol | FL/FR |
| dextro,laevo- | borneol | FL/FR |
| dextro- | borneol | FL/FR |
| iso | bornyl formate | FL/FR |
| iso | bornyl methyl ether | FL/FR |
| iso | bornyl propionate | FL/FR |
| | cinnamyl formate | FL/FR |
| dextro- | fenchone | FL/FR |
| | fir needle oil siberia | FL/FR |
| | hexyl benzoate | FL/FR |
| camphoreous |
| | bornyl ethyl ether | |
| 2,6- | dimethyl-3-oxatricyclo(4.2.1.0*2,4*)nonane | FR |
| | fenchol | FL/FR |
| laevo- | fenchone | FL/FR |
| | hinoki leaf oil | FR |
| | melaleuca viridiflora leaf oil | FR |
| chocolate |
| 1,3,3,4,5,6- | hexamethyl(2.2.2)bicyclooct-5-en-2-ol | |
| citrus |
| (E+Z)-4,8- | dimethyl-3,7-nonadien-2-yl acetate | FL/FR |
| | petitgrain combava oil | FR |
| clean |
| | cyclododecyl formate | FR |
| earthy |
| 2- | octanone oxime | FR |
| ethereal |
| | ethyl 4-pentenoate | FL/FR |
| fatty |
| (E)-2- | octenal | FL/FR |
| floral |
| | bois de rose oil peru | FL/FR |
| | dihydro-alpha-ionone | FL/FR |
| | dihydrorose oxide | FR |
| | dimethyl benzyl carbinyl butyrate | FL/FR |
| | geranium oil africa | FL/FR |
| | geranium oil egypt | FL/FR |
| | ho leaf oil | FR |
| | lavender oil | FL/FR |
| | linalool oxide | FL/FR |
| 2- | pentyl cyclopentanone | FR |
| | rose pyran | FR |
| fruity |
| 3- | allyl oxy-1,4-dimethyl bicyclo(3.2.1)octane | FR |
| 1,3,3,5- | tetramethyl-7 and 8-acetyl bicyclo(2.2.2)oct-5-ene | |
| | tropical indene | FR |
| green |
| iso | butyl heptanoate | FL/FR |
| iso | butyl methyl ketone | FL/FR |
| 2-sec- | butyl thiazole | FL/FR |
| iso | cyclocitral (IFF) | FL/FR |
| | fern absolute | |
| | galbanum oil | FL/FR |
| | heptanal (aldehyde C-7) | FL/FR |
| (E)-4- | hexen-1-ol | |
| (Z)-4- | hexen-1-ol | FL/FR |
| 3- | hexenyl 2-methyl butyrate | FL/FR |
| english | ivy leaf absolute | FR |
| | seaweed absolute (fucus vesiculosus et serratus) | FL/FR |
| 1- | allyl-2,2,7,7-tetramethyl cycloheptanol | FR |
| 1,4- | cineole | FL/FR |
| 1,8- | cineole | FL/FR |
| ortho- | cresyl salicylate | FL/FR |
| | dimethyl cyclormol (IFF) | FR |
| | geranic oxide | FL/FR |
| cis- | herbal cyclohexane | FR |
| | herbal dioxane | FR |
| | herbal undecane | FR |
| 6- | hydroxydihydrotheaspirane (mixture of isomers) | FL/FR |
| | hyssop oil | FL/FR |
| spike | lavender oil | FL/FR |
| spike | lavender oil spain | FL/FR |
| | linalyl formate | FL/FR |
| | melaleuca leucadendron cajaputi oil | FL/FR |
| | melaleuca leucadendron var. cajuputi leaf oil | FL/FR |
| | melaleuca linariifolia oil | FR |
| | melaleuca quinquenervia water | FR |
| para- | menthane-3,8-diol | FL/FR |
| | methyl cyclogeranate (Firmenich) | FR |
| (E)-6- | methyl-3-hepten-2-one | FL/FR |
| | niaouli oil | FR |
| | nonisyl formate | FR |
| 1- | octen-3-yl acetate | FL/FR |
| | origanum oil | FL/FR |
| | origanum oil greece | FL/FR |
| | perillaldehyde | FL/FR |
| | pine hexanol | FR |
| alpha- | pinene | FL/FR |
| | rosemary absolute | FL/FR |
| | rosemary oil | FL/FR |
| | rosemary oil africa | FL/FR |
| | rosemary oil morocco | FL/FR |
| | rosemary oil spain | FL/FR |
| | rosemary oil tunisia | FL/FR |
| | rosemary specialty | FR |
| | sabinene hydrate | FL/FR |
| | tagete oil CO2 extract | FL/FR |
| | tagete oil south africa | FL/FR |
| | terpineols (unspec.) (mixed isomers) | FL/FR |
| | viridiflorol | FL/FR |
| laevo- | menthol | FL/FR |
| | peppermint cyclohexanone | FL/FR |
| minty |
| 5- and 6-iso | propyl-1,3,3-trimethyl bicyclo(2.2.2)-5,7-octadien-2-one | |
| (-)-iso | pulegol | FL/FR |
| mossy |
| | oakmoss absolute | FL/FR |
| musk |
| | acetyl ethyl tetramethyl tetralin replacer | FR |
| naphthyl |
| para- | methyl anisole | FL/FR |
| spicy |
| 4- | carvomenthenol | FL/FR |
| | cuminaldehyde | FL/FR |
| | elettaria cardamomum seed oil | FL/FR |
| | marjoram oil (thymus mastichina) spain | FL/FR |
| white | sassafras oil | FL/FR |
| terpenic |
| | cypress leaf oil | FR |
| thujonic |
| | cedarleaf oil terpeneless | FR |
| | sage oil (salvia lavandulifolia vahl.) spain | FL/FR |
| | sage oil dalmatian | FL/FR |
| woody |
| iso | bornyl isovalerate | FL/FR |
| 2-tert- | butyl cyclohexanone | FR |
| | camphene | FL/FR |
| epoxidized | cedarwood oil | FR |
| | cyperus root oil (cyperus scariosus) | FR |
| | dihydro-beta-ionone | FL/FR |
| | germacrene B | |
| 1,2,3,3,4,5,6- | heptamethyl bicyclo(2.2.2)oct-5-en-2-ol | |
| | herbal norbornane | FR |
| | hinoki root oil | FR |
| | indisan (IFF) | FR |
| | juniper berry oil terpenes | FR |
| | orris hexanone | FR |
| | pinacol | FR |
| | sandal cyclohexanol | FR |
| | sandela | FR |
| | santall | FR |
| beta- | terpineol | FL/FR |
| 1,3,3,5- | tetramethyl-7 and 8-cyanobicyclo(2.2.2)oct-5-ene | |
| alpha- | thujene | |
| | verdoxan | FR |
| | vetiver oil haiti | FL/FR |
| | woody octene | FR |
| | zedoary bark oil | FL/FR |
| |
| For Flavor |
| |
| No flavor group found for these |
| dextro,laevo- | borneol | FL/FR |
| dextro- | borneol | FL/FR |
| iso | bornyl methyl ether | FL/FR |
| iso | butyl heptanoate | FL/FR |
| 4- | butyl thiazole | FL |
| 2-sec- | butyl thiazole | FL/FR |
| ortho- | cresyl salicylate | FL/FR |
| (E+Z)-4,8- | dimethyl-3,7-nonadien-2-yl acetate | FL/FR |
| | ethyl 4-pentenoate | FL/FR |
| | fern absolute | |
| | fig leaf absolute | FL |
| | germacrene B | |
| 1,2,3,3,4,5,6- | heptamethyl bicyclo(2.2.2)oct-5-en-2-ol | |
| (E,E)-2,4- | hexadien-1-ol | FL |
| 1,3,3,4,5,6- | hexamethyl(2.2.2)bicyclooct-5-en-2-ol | |
| | linalyl formate | FL/FR |
| | melaleuca leucadendron var. cajuputi leaf oil | FL/FR |
| para- | menthane-3,8-diol | FL/FR |
| (E)-6- | methyl-3-hepten-2-one | FL/FR |
| 2- | propyl thiazole | FL |
| 5- and 6-iso | propyl-1,3,3-trimethyl bicyclo(2.2.2)-5,7-octadien-2-one | |
| white | sassafras oil | FL/FR |
| | seaweed absolute (fucus vesiculosus et serratus) | FL/FR |
| | tagete oil rwanda | |
| beta- | terpineol | FL/FR |
| | terpineols (unspec.) (mixed isomers) | FL/FR |
| 1,3,3,5- | tetramethyl-7 and 8-acetyl bicyclo(2.2.2)oct-5-ene | |
| 1,3,3,5- | tetramethyl-7 and 8-cyanobicyclo(2.2.2)oct-5-ene | |
| alpha- | thujene | |
| | viridiflorol | FL/FR |
| balsamic |
| iso | bornyl propionate | FL/FR |
| | fir needle oil siberia | FL/FR |
| berry |
| | dihydro-alpha-ionone | FL/FR |
| camphoreous |
| laevo- | borneol | FL/FR |
| | bornyl ethyl ether | |
| | camphene | FL/FR |
| | fenchol | FL/FR |
| laevo- | fenchone | FL/FR |
| | geranic oxide | FL/FR |
| 6- | hydroxydihydrotheaspirane (mixture of isomers) | FL/FR |
| | rosemary oil tunisia | FL/FR |
| cooling |
| 4- | carvomenthenol | FL/FR |
| 1,4- | cineole | FL/FR |
| dextro- | fenchone | FL/FR |
| spike | lavender oil | FL/FR |
| laevo- | menthol | FL/FR |
| iso | menthol | FL |
| | sabinene hydrate | FL/FR |
| fatty |
| (E)-2- | octenal | FL/FR |
| floral |
| | bois de rose oil peru | FL/FR |
| | dimethyl benzyl carbinyl butyrate | FL/FR |
| | geranium oil africa | FL/FR |
| | geranium oil egypt | FL/FR |
| fruity |
| | tagete oil CO2 extract | FL/FR |
| | tagete oil south africa | FL/FR |
| green |
| iso | butyl methyl ketone | FL/FR |
| iso | cyclocitral (IFF) | FL/FR |
| | galbanum oil | FL/FR |
| | heptanal (aldehyde C-7) | FL/FR |
| (E)-4- | hexen-1-ol | |
| (Z)-4- | hexen-1-ol | FL/FR |
| 3- | hexenyl 2-methyl butyrate | FL/FR |
| | hexyl benzoate | FL/FR |
| | linalool oxide | FL/FR |
| | oakmoss absolute | FL/FR |
| 1- | octen-3-yl acetate | FL/FR |
| herbal |
| 2- | acetoxy-1,8-cineole | FL |
| | hyssop oil | FL/FR |
| | lavender oil | FL/FR |
| spike | lavender oil spain | FL/FR |
| | melaleuca leucadendron cajaputi oil | FL/FR |
| | origanum oil | FL/FR |
| | origanum oil greece | FL/FR |
| | rosemary absolute | FL/FR |
| | rosemary oil | FL/FR |
| | rosemary oil africa | FL/FR |
| | rosemary oil morocco | FL/FR |
| | rosemary oil spain | FL/FR |
| | sage oil (salvia lavandulifolia vahl.) spain | FL/FR |
| licorice |
| | estragole | FL/FR |
| mentholic |
| | peppermint cyclohexanone | FL/FR |
| minty |
| 1,8- | cineole | FL/FR |
| (-)-iso | pulegol | FL/FR |
| naphthyl |
| para- | methyl anisole | FL/FR |
| spicy |
| | cinnamyl formate | FL/FR |
| | cuminaldehyde | FL/FR |
| | elettaria cardamomum seed oil | FL/FR |
| | marjoram oil (thymus mastichina) spain | FL/FR |
| | perillaldehyde | FL/FR |
| | turmeric oleoresin | FL |
| terpenic |
| para- | menthatriene | FL |
| thujonic |
| | sage oil dalmatian | FL/FR |
| woody |
| iso | bornyl formate | FL/FR |
| iso | bornyl isovalerate | FL/FR |
| | dihydro-beta-ionone | FL/FR |
| alpha- | pinene | FL/FR |
| | vetiver oil haiti | FL/FR |
| | zedoary bark oil | FL/FR |
| |
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | bicyclo(2.2.1)heptan-2-ol, 1,3,3-trimethyl-, (1S-endo)- | | 2-nor | bornanol, 1,3,3-trimethyl-, (-)-endo- | | (-)-alpha- | fenchol | | (-)-alpha- | fenchyl alcohol | | L-alpha- | fenchyl alcohol | | laevo-alpha- | fenchyl alcohol | | | trimethyl bicyclo-2-heptanol | | (1S-endo)-1,3,3- | trimethyl bicyclo(2.2.1)heptan-2-ol | | (1S,2S,4R)-1,3,3- | trimethyl bicyclo(2.2.1)heptan-2-ol | | (1S-endo)-1,3,3- | trimethyl-2-norbornanol | | 1,3,3- | trimethyl-2-norbornanol, (1S-endo)- | | (1S-endo)-1,3,3- | trimethylbicyclo(2.2.1)heptan-2-ol | | (1S,2S,4R)-1,3,3- | trimethylbicyclo[2.2.1]heptan-2-ol |
Articles:
| PubMed: | Kinetics and mechanisms of the tropospheric reactions of menthol, borneol, fenchol, camphor, and fenchone with hydroxyl radicals (OH) and chlorine atoms (Cl). |
| PubMed: | Fragrance material review on fenchyl alcohol. |
| PubMed: | Roles of human CYP2A6 and rat CYP2B1 in the oxidation of (+)-fenchol by liver microsomes. |
| PubMed: | Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of linalyl pyrophosphate to (-)-endo-fenchol. |
| PubMed: | Biosynthesis of monoterpenes. Stereochemistry of the enzymatic cyclization of geranyl pyrophosphate to (-)-endo-fenchol. |
| PubMed: | Monoterpene biosynthesis: mechanistic evaluation of the geranyl pyrophosphate:(-)-endo-fenchol cyclase from fennel (Foeniculum vulgare). |
| PubMed: | Chemical composition and bioactivity of different oregano (Origanum vulgare) extracts and essential oil. |
| PubMed: | Chemical analysis and biological activity of the essential oils of two endemic Soqotri Commiphora species. |
| PubMed: | Inhibitory effects of monoterpenes on human TRPA1 and the structural basis of their activity. |
| PubMed: | Biosynthesis of monoterpenes: conversion of the acyclic precursors geranyl pyrophosphate and neryl pyrophosphate to the rearranged monoterpenes fenchol and fenchone by a soluble enzyme preparation from fennel (Foeniculum vulgare). |
| PubMed: | Biosynthesis of monoterpenes: preliminary characterization of i-endo-fenchol synthetase from fennel (Foeniculum vulgare) and evidence that no free intermediate is involved in the cyclization of geranyl pyrophosphate to the rearranged product. |
| PubMed: | A superior P-H phosphonite: asymmetric allylic substitutions with fenchol-based palladium catalysts. |
| PubMed: | Antioxidant and antimicrobial properties of the essential oil and extracts of Zanthoxylum alatum grown in north-western Himalaya. |
| PubMed: | Phosphinofenchol or metastable phosphorane? Phosphorus derivatives of fenchol. |
| PubMed: | [GC-MS analysis of chemical components in seeds oil from Croton tiglium]. |
| PubMed: | Distillation time effect on lavender essential oil yield and composition. |
| PubMed: | Electrophysiological and behavioral responses of the bark beetle Dendroctonus rhizophagus to volatiles from host pines and conspecifics. |
| PubMed: | GC and GC/MS analysis of essential oil composition of the endemic Soqotraen Leucas virgata Balf.f. and its antimicrobial and antioxidant activities. |
| PubMed: | Grapevine bunch rots: impacts on wine composition, quality, and potential procedures for the removal of wine faults. |
| PubMed: | Fumigant toxicity and oviposition deterrency of the essential oil from cardamom, Elettaria cardamomum, against three stored–product insects. |
| PubMed: | Comparison of volatile constituents, and antioxidant and antibacterial activities of the essential oils of Thymus caucasicus, T. kotschyanus and T. vulgaris. |
| PubMed: | Structure of 2-methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a noncanonical C-methylated monoterpenoid substrate. |
| PubMed: | Effects of the origins of Botrytis cinerea on earthy aromas from grape broth media further inoculated with Penicillium expansum. |
| PubMed: | Variation in volatile leaf oils of five Eucalyptus species harvested from Jbel Abderrahman arboreta (Tunisia). |
| PubMed: | Microextraction and Gas Chromatography/Mass Spectrometry for improved analysis of geosmin and other fungal "off" volatiles in grape juice. |
| PubMed: | Chemical diversity in the genus Alpinia (Zingiberaceae): comparative composition of four Alpinia species grown in Northern India. |
| PubMed: | Effect of various essential oils isolated from Douglas fir needles upon sheep and deer rumen microbial activity. |
| PubMed: | Compositional variability in essential oil from different parts of Alpinia speciosa from India. |
| PubMed: | NIR-VCD, vibrational circular dichroism in the near-infrared: experiments, theory and calculations. |
| PubMed: | Electrophysiological and behavioral responses of Dendroctonus frontalis (Coleoptera: Curculionidae) to volatiles isolated from conspecifics. |
| PubMed: | Acetophenone as an anti-attractant for the western pine beetle, Dendroctonus Brevicomis LeConte (Coleoptera: Scolytidae). |
| PubMed: | Odor thresholds of microbially induced off-flavor compounds in apple juice. |
| PubMed: | Phytochemical investigation and evaluation of anti-inflammatory and anti-arthritic activities of essential oil of Strobilanthus ixiocephala Benth. |
| PubMed: | Olfactory sensitivity of two sympatric species of rice leaf folders (Lepidoptera: Pyralidae) to plant volatiles. |
| PubMed: | Monoterpenes as drug shuttles: cytotoxic (6-aminomethylnicotinate)dichloridoplatinum(II) complexes with potential to overcome cisplatin resistance. |
| PubMed: | Determination of essential oil components of Artemisia haussknechtii Boiss. using simultaneous hydrodistillation-static headspace liquid phase microextraction-gas chromatography mass spectrometry. |
| PubMed: | Composition and antimalarial activity in vitro of the essential oil of Tetradenia riparia. |
| PubMed: | Screening of antibacterial activities of twenty-one oxygenated monoterpenes. |
| PubMed: | Olfactory discrimination of structurally related molecules: receptor cell responses to camphoraceous odorants. |
| PubMed: | Sensitive indoor air monitoring of monoterpenes using different adsorbents and thermal desorption gas chromatography with mass-selective detection. |
| PubMed: | Rationalization of enantioselectivities in dialkylzinc additions to benzaldehyde catalyzed by fenchone derivatives. |
| PubMed: | Volatile compounds in the larval frass ofDendroctonus valens andDendroctonus micans (Coleoptera: Scolytidae) in relation to oviposition by the predator,Rhizophagus grandis (Coleoptera: Rhizophagidae). |
| PubMed: | [GC-MS analysis and inhibitory activity of the essential oil extracted from the leaves of Lindera communis]. |
| PubMed: | Rapid headspace solid-phase microextraction/gas chromatographic/mass spectrometric assay for the quantitative determination of some of the main odorants causing off-flavours in wine. |
| PubMed: | A dispensable methoxy group? Phenyl fencholate as a chiral modifier of n-butyllithium. |
| PubMed: | Relationships between odor-elicited oscillations in the salamander olfactory epithelium and olfactory bulb. |
| PubMed: | Characterisation of volatile organic compounds in stemwood using solid-phase microextraction. |
|