farnesal
3,7,11-trimethyl-2,6,10-dodecatrienal
Identification
| Name | farnesal |
| IUPAC | 3,7,11-trimethyldodeca-2,6,10-trienal |
| CAS Number | 19317-11-4 |
| EINECS | 242-957-9 |
| FDA UNII | R265G157TQ |
| Molecular Formula | C15 H24 O |
| Molecular Weight | 220.35548000 |
| MDL Number | MFCD00038089 |
| Beilstein | 1723427 |
| CoE Number | 5148 |
Regulatory
| JECFA Food Flavoring | 1228 3,7,11-trimethyl-2,6,10-dodecatrienal |
| DG SANTE Food Flavourings | 05.148 farnesal |
| FEMA Number | 4019 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 19317-11-4 ; FARNESAL |
Physical Properties
| Appearance | pale yellow to yellow clear liquid (est) |
| Assay | 99.00 to 100.00 sum of isomers |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.89000 to 0.90000 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.406 to 7.489 |
| Refractive Index | 1.49400 to 1.50400 @ 20.00 °C. |
| Boiling Point | 126.00 to 129.00 °C. @ 3.50 mm Hg, 198.00 to 201.00 °C. @ 8.00 mm Hg |
| Acid Value | 3.00 max. KOH/g |
| Vapor Pressure | 0.000187 mmHg @ 25.00 °C. (est) |
| Flash Point | > 212.00 °F. TCC ( > 100.00 °C. ) |
| logP (o/w) | 5.013 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Description | at 100.00 %. |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| 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 |
| IFRA Critical Effect | Dermal sensitization and systemic toxicity |
| IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%) | Category 1: Products applied to the lips |
| Notes | IFRA FLAVOR REQUIREMENTS: |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.49 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 0.20 (μg/capita/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| baked goods | 2.00000 |
| beverages(nonalcoholic) | 0.10000 |
| beverages(alcoholic) | 0.30000 |
| breakfast cereal | 0.10000 |
| cheese | - |
| chewing gum | 2.00000 |
| condiments / relishes | - |
| confectionery froastings | 0.30000 |
| egg products | 0.30000 |
| fats / oils | 0.30000 |
| fish products | - |
| frozen dairy | 0.50000 |
| fruit ices | 0.20000 |
| gelatins / puddings | 0.20000 |
| granulated sugar | - |
| gravies | 0.30000 |
| hard candy | 0.50000 |
| imitation dairy | - |
| instant coffee / tea | 0.10000 |
| jams / jellies | 0.50000 |
| meat products | - |
| milk products | 0.20000 |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | 0.50000 |
| snack foods | 0.50000 |
| soft candy | 0.50000 |
| soups | 0.10000 |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
farnesal, pract.
3,7,11-
trimethyl dodeca-2,6,10-trienone
3,7,11-
trimethyl-2,6,10-dodecatrienal
3,7,11-
trimethyldodeca-2,6,10-trienal
PubMed:
Aldoketoreductase family 1B10 (AKR1B10) as a biomarker to distinguish hepatocellular carcinoma from benign liver lesions.
PubMed:
Cloning and characterization of four rabbit aldo-keto reductases featuring broad substrate specificity for xenobiotic and endogenous carbonyl compounds: relationship with multiple forms of drug ketone reductases.
PubMed:
Farnesyl phosphatase, a Corpora allata enzyme involved in juvenile hormone biosynthesis in Aedes aegypti.
PubMed:
Aldehyde dehydrogenase 3 converts farnesal into farnesoic acid in the corpora allata of mosquitoes.
PubMed:
Naphthyl groups in chiral recognition: structures of salts and esters of 2-methoxy-2-naphthylpropanoic acids.
PubMed:
Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis.
PubMed:
Moths behaving like butterflies. Evolutionary loss of long range attractant pheromones in castniid moths: a Paysandisia archon model.
PubMed:
Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10.
PubMed:
Overexpression and oncogenic function of aldo-keto reductase family 1B10 (AKR1B10) in pancreatic carcinoma.
PubMed:
Identification, functional characterization, and regulation of the enzyme responsible for floral (E)-nerolidol biosynthesis in kiwifruit (Actinidia chinensis).
PubMed:
A coordinated expression of biosynthetic enzymes controls the flux of juvenile hormone precursors in the corpora allata of mosquitoes.
PubMed:
Roles of rat and human aldo-keto reductases in metabolism of farnesol and geranylgeraniol.
PubMed:
Rat aldose reductase-like protein (AKR1B14) efficiently reduces the lipid peroxidation product 4-oxo-2-nonenal.
PubMed:
Identification of a novel abscisic acid-regulated farnesol dehydrogenase from Arabidopsis.
PubMed:
2,3-Dihydrohomofarnesal: female sex attractant pheromone component of Callosobruchus rhodesianus (Pic).
PubMed:
Chromene-3-carboxamide derivatives discovered from virtual screening as potent inhibitors of the tumour maker, AKR1B10.
PubMed:
Farnesylcysteine lyase is involved in negative regulation of abscisic acid signaling in Arabidopsis.
PubMed:
NADP+-dependent farnesol dehydrogenase, a corpora allata enzyme involved in juvenile hormone synthesis.
PubMed:
Kinetic studies of AKR1B10, human aldose reductase-like protein: endogenous substrates and inhibition by steroids.
PubMed:
Homofarnesals: female sex attractant pheromone components of the southern cowpea weevil, Callosobruchus chinensis.
PubMed:
Zeolite NaY-promoted cyclization of farnesal: a short route to nanaimoal.
PubMed:
Enzymatic characteristics of an aldo-keto reductase family protein (AKR1C15) and its localization in rat tissues.
PubMed:
Arabidopsis thaliana plants possess a specific farnesylcysteine lyase that is involved in detoxification and recycling of farnesylcysteine.
PubMed:
A facile phenol-driven intramolecular diastereoselective thermal/base-catalyzed dipolar [2+2] annulation reactions: an easy access to complex bioactive natural and unnatural benzopyran congeners.
PubMed:
The retinoid-X receptor ortholog, ultraspiracle, binds with nanomolar affinity to an endogenous morphogenetic ligand.
PubMed:
A modular and concise total synthesis of (+/-)-daurichromenic acid and analogues.
PubMed:
Absolute configuration of chiral terpenes in marking pheromones of bumblebees and cuckoo bumblebees.
PubMed:
Chemical ecology of oribatid mites III. Chemical composition of oil gland exudates from two oribatid mites, Trhypochthoniellus sp. and Trhypochthonius japonicus (Acari: Trhypochthoniidae).
PubMed:
Juvenile hormone biosynthesis in moths: synthesis and evaluation of farnesol homologs as alternate substrates of farnesol oxidase.
PubMed:
A novel, inducible, citral lyase purified from spores of Penicillium digitatum.
PubMed:
Alpha-phosphono lactone analogues of farnesyl pyrophosphate: an asymmetric synthesis via ring-closing metathesis.
PubMed:
Study on the biosynthesis of dolichol in yeast: recognition of the prenyl chain length in polyprenol reduction.
PubMed:
Farnesol oxidation in insects: evidence that the biosynthesis of insect juvenile hormone is mediated by a specific alcohol oxidase.
PubMed:
Lysosomal prenylcysteine lyase is a FAD-dependent thioether oxidase.
PubMed:
Neuropeptide regulation of biosynthesis of the juvenoid, methyl farnesoate, in the edible crab, Cancer pagurus.
PubMed:
Phosphonate and bisphosphonate analogues of farnesyl pyrophosphate as potential inhibitors of farnesyl protein transferase.
PubMed:
Substrate specificity for the epoxidation of terpenoids and active site topology of house fly cytochrome P450 6A1.
PubMed:
Lipoperoxidase activity of Pityrosporum: characterisation of by-products and possible rôle in pityriasis versicolor.
PubMed:
A model for farnesoid feedback control in the mevalonate pathway.
PubMed:
Formation of farnesal and 3-hydroxy-2,3-dihydrofarnesal from farnesol by protoplasts of Botryococcus braunii.
PubMed:
Hormonal effects on insects and other endoparasites in vitro.
PubMed:
Identification of thoracic gland constituents from maleXylocopa spp. latreille (Hymenoptera: Anthophoridae) from arizona.
PubMed:
Sex pheromones of rice moth,Corcyra cephalonica Stainton : I. Identification of male pheromone.
PubMed:
Farnesol and farnesal dehydrogenase(s) in corpora allata of the tobacco hornworm moth, Manduca sexta.
PubMed:
Soldier-specific chemicals of the termiteCurvitermes strictinasus Mathews (Isoptera, Nasutitermitinae).
PubMed:
The in vitro effects of farnesol and derivatives on Hymenolepis diminuta.
PubMed:
[Juvenile hormone in diapausing Pieris brassicae and mutations. Tetrahydrofolic acid and pterins incubated in chrysalids, provoking ontogenic and mutagenic genetic information alterations in Drosophila melanogaster].