EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

farnesal
3,7,11-trimethyl-2,6,10-dodecatrienal

Supplier Sponsors

Name:3,7,11-trimethyldodeca-2,6,10-trienal
CAS Number: 19317-11-4Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:242-957-9
FDA UNII:R265G157TQ
Beilstein Number:1723427
MDL:MFCD00038089
CoE Number:5148
XlogP3-AA:4.90 (est)
Molecular Weight:220.35548000
Formula:C15 H24 O
NMR Predictor:Predict (works with chrome or firefox)
EFSA/JECFA Comments:
Mixture of (Z)- and (E)-isomer for both C=C double bonds (EFFA, 2010). 10-15 % (2Z,6Z); 20-25 % (2E,6Z); 20-25% (2Z,6E); 40-50 % (2E,2E) (EFFA, 2013).
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
JECFA Food Flavoring:1228 3,7,11-trimethyl-2,6,10-dodecatrienal
FLAVIS Number:05.148 (Old)
DG SANTE Food Flavourings:05.148 farnesal
FEMA Number:4019 3,7,11-trimethyl-2,6,10-dodecatrienal
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
Boiling Point: 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
 water, 0.4278 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Strength:medium
Odor Description:at 100.00 %. floral minty
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
 
Suppliers:
BOC Sciences
For experimental / research use only.
FARNESAL ≥85%
Frinton Laboratories
For experimental / research use only.
Farnesal, Pract.
Parchem
farnesal
Penta International
FARNESAL
Santa Cruz Biotechnology
For experimental / research use only.
Farnesal
Sigma-Aldrich
Farnesal, mixture of isomers, ≥85%
Certified Food Grade Products
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
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
Recommendation for farnesal usage levels up to:
  6.0000 % in the fragrance concentrate.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.49 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.20 (μg/capita/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 20
 average usual ppmaverage maximum ppm
baked goods: 2.0000010.00000
beverages(nonalcoholic): 0.100000.80000
beverages(alcoholic): 0.300002.00000
breakfast cereal: 0.100000.80000
cheese: --
chewing gum: 2.0000015.00000
condiments / relishes: --
confectionery froastings: 0.300002.00000
egg products: 0.300002.00000
fats / oils: 0.300002.00000
fish products: --
frozen dairy: 0.500006.00000
fruit ices: 0.200002.10000
gelatins / puddings: 0.200002.00000
granulated sugar: --
gravies: 0.300002.00000
hard candy: 0.500005.00000
imitation dairy: --
instant coffee / tea: 0.100001.00000
jams / jellies: 0.500005.00000
meat products: --
milk products: 0.200002.10000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 0.500005.00000
snack foods: 0.500005.00000
soft candy: 0.500005.00000
soups: 0.100000.80000
sugar substitutes: --
sweet sauces: --
 
Safety References:
European Food Safety Athority(efsa):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 202: 3-Alkylated aliphatic acyclic alpha,beta-unsaturated aldehydes and precursors with or without additional double bonds from chemical subgroup 1.1.3 of FGE.19[1]
View page or View pdf

Flavouring Group Evaluation 72 (FGE.72): Consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids, and related esters evaluated by the JECFA (61st meeting) structurally related to branched- and straight-chain unsaturated carboxylic acids. Esters of these and straight-chain aliphatic saturated alcohols evaluated by EFSA in FGE.05Rev2 (2010)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 72, Revision 1 (FGE.72Rev1): Consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids, and related esters evaluated by the JECFA (61st meeting) structurally related to branched- and straight-chain unsaturated carboxylic acids, esters of these and straight-chain aliphatic saturated alcohols evaluated by EFSA in FGE.05Rev2
View page or View pdf

EPI System: View
NLM Developmental and Reproductive Toxicity:Search
EPA Substance Registry Services (TSCA):19317-11-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :68150
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
3,7,11-trimethyldodeca-2,6,10-trienal
Chemidplus:0019317114
 
References:
 3,7,11-trimethyldodeca-2,6,10-trienal
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:19317-11-4
Pubchem (cid):68150
Pubchem (sid):135043794
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
KEGG (GenomeNet):C03461
HMDB (The Human Metabolome Database):HMDB60356
FooDB:FDB014515
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
For Odor
aldehydic
iso
butyraldehyde
FL/FR
floral
cyclohexyl propanol
FR
earthy indane
FR
floral methanol
FR
ylang ylang flower oil CO2 extract
FL/FR
ylang ylang flower oil I
FL/FR
ylang ylang flower oil II
FL/FR
ylang ylang flower oil III
FL/FR
minty
dihydrocarveol
FL/FR
For Flavor
aldehydic
iso
butyraldehyde
FL/FR
floral
ylang ylang flower oil CO2 extract
FL/FR
ylang ylang flower oil I
FL/FR
ylang ylang flower oil II
FL/FR
ylang ylang flower oil III
FL/FR
green
dihydrocarveol
FL/FR
 
Potential Uses:
FRfloral
FRjasmin
FRnarcissus
FRneroli
FRrose
FRtuberose
 
Occurrence (nature, food, other):note
 ginger rhizome
Search Trop Picture
 ginger rhizome oil
Search Trop Picture
 lemongrass plant
Search Trop Picture
 tomato fruit
Search Trop Picture
 
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
 

Articles:

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].
 
Notes:
None found
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