farnesyl acetone
2,6,10-trimethyl-2,6,10-pentadecatrien-14-one
Identification
| Name | farnesyl acetone |
| IUPAC | 6,10,14-trimethylpentadeca-5,9,13-trien-2-one |
| CAS Number | 762-29-8 |
| EINECS | 212-097-9 |
| FDA UNII | 26A08O86E6 |
| Molecular Formula | C18 H30 O |
| Molecular Weight | 262.43630000 |
| MDL Number | MFCD00036517 |
| Beilstein | 1781239 |
| CoE Number | 11206 |
Regulatory
| JECFA Food Flavoring | 1123 2,6,10-trimethyl-2,6,10-pentadecatrien-14-one |
| DG SANTE Food Flavourings | 07.114 6,10,14-trimethylpentadeca-5,9,13-trien-2-one |
| FEMA Number | 3442 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 762-29-8 ; 2,6,10-TRIMETHYL-2,6,10-PENTADECATRIEN-14-ONE |
Physical Properties
| Appearance | pale greenish yellow clear liquid (est) |
| Assay | 96.00 to 100.00 sum of isomers |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.88500 to 0.89500 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.364 to 7.447 |
| Refractive Index | 1.47800 to 1.48300 @ 20.00 °C. |
| Boiling Point | 147.00 to 148.00 °C. @ 0.50 mm Hg, 302.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.000009 mmHg @ 25.00 °C. (est) |
| Flash Point | 230.00 °F. TCC ( 110.00 °C. ) |
| logP (o/w) | 5.721 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Description |
at 100.00 %. Fruity, wine-like, somewhat floral
|
| Taste Description | winey |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 [sex: M,F] > 5000 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for farnesyl acetone usage levels up to | 5.0000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.085 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | ND (μg/capita/day) |
| Threshold of Concern | 540 (μg/person/day) |
| Structure Class | II |
| baked goods | - |
| beverages(nonalcoholic) | - |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
farnesylacetone
6,10,14-
trimethyl pentadeca-5,9,13-trien-2-one
trimethyl pentadecatrien-2-one
2,6,10-
trimethyl-2,6,10-pentadecatrien-14-one
6,10,14-
trimethyl-5,9,13-pentadecatrien-2-one
6,10,14-
trimethylpentadeca-5,9,13-trien-2-one
PubMed:
Tomato carotenoid cleavage dioxygenases 1A and 1B: Relaxed double bond specificity leads to a plenitude of dialdehydes, mono-apocarotenoids and isoprenoid volatiles.
PubMed:
Formation of norisoprenoid flavor compounds in carrot (Daucus carota L.) roots: characterization of a cyclic-specific carotenoid cleavage dioxygenase 1 gene.
PubMed:
5E- and 5Z-farnesylacetones from Sargassum siliquastrum as novel selective L-type calcium channel blockers.
PubMed:
Phytochemical analysis and allelopathic activity of essential oils of Ecballium elaterium A. Richard growing in Iran.
PubMed:
Vasodilatation effect of farnesylacetones, active constituents of Sargassum siliquastrum, on the basilar and carotid arteries of rabbits.
PubMed:
Linear and cyclic C18 terpenoids from the southern Australian marine brown alga Cystophora moniliformis.
PubMed:
COX-1, COX-2 inhibitors and antifungal agents from Croton hutchinsonianus.
PubMed:
Isolation and characterization of a monoamine oxidase B selective inhibitor from tobacco smoke.
PubMed:
Identification of oxidation products of solanesol produced during air sampling for tobacco smoke by electrospray mass spectrometry and HPLC.
PubMed:
Carotenoid pigmentation affects the volatile composition of tomato and watermelon fruits, as revealed by comparative genetic analyses.
PubMed:
Cholinesterase inhibitory activity of two farnesylacetone derivatives from the brown alga Sargassum sagamianum.
PubMed:
Studies on the interactions of tobacco leaf and tobacco smoke constituents and monoamine oxidase.
PubMed:
Analysis of free and bound volatiles by gas chromatography and gas chromatography-mass spectrometry in uncased and cased tobaccos.
PubMed:
Modulation of membrane fluidity and lipidic metabolism in transformed rat fibroblasts induced by the sesquiterpenic hormone farnesylacetone.
PubMed:
Farnesylacetone, a sesquiterpenic hormone of Crustacea, inhibits electron transport in isolated rat liver mitochondria.
PubMed:
Comparative effect of farnesylacetone on macromolecular synthesis in gonads of crustaceans.
PubMed:
Inhibition of transmethylases by unsaturated carbonyl derivatives.
PubMed:
[In vitro inhibition of tRNA methyltransferases by queen substance, a pheromone of queen honeybees].
PubMed:
Anticonvulsant activity of farnesylacetone epoxide--a novel marine natural product.
PubMed:
[Inhibition of biological methylations by t,t-farnesylacetone, a constituant of the androgenic gland of the male crab, Carcinus maenas].
PubMed:
[The quantitative composition of natural and technologically changed aromas of plants. IV. Enzymic and thermal reaction products formed during the processing of tomatoes (author's transl)].
PubMed:
6,10,14-Trimethylpentadecan-2-one and 6,10,14-trimethyl-5-trans, 9-trans, 13-pentadecatrien-2-one from the androgenic glands of the male crab Carcinus maenas.