| Name: | 3,7,11-trimethyldodeca-2,6,10-trienal |
| CAS Number: | 19317-11-4 |  3D/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, Edge 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:
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 Description:at 100.00 %. floral minty |
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
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 |
| RIFM Fragrance Material Safety Assessment: Search |
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice |
| IFRA Critical Effect: | | Dermal sensitization and systemic toxicity |
| | View the IFRA Standard |
| View IFRA Standards Library for complete information. |
| Please review Amendment 49 IFRA documentation for complete information. |
| IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%): |
| Category 1: Products applied to the lips |
| 0.11 % |
| Category 2: Products applied to the axillae |
| 0.032 % |
| Category 3: Products applied to the face/body using fingertips |
| 0.11 % |
| Category 4: Products related to fine fragrance |
| 0.60 % |
| | Category 5: Products applied to the face and body using the hands (palms), primarily leave-on |
| Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on |
| 0.15 % |
| Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on |
| 0.15 % |
| Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on |
| 0.15 % |
| Category 5D: Baby Creams, baby Oils and baby talc |
| 0.051 % |
| Category 6: Products with oral and lip exposure |
| 0.11 % |
| | Category 7: Products applied to the hair with some hand contact |
| Category 7A: Rinse-off products applied to the hair with some hand contact |
| 0.34 % |
| Category 7B: Leave-on products applied to the hair with some hand contact |
| 0.34 % |
| Category 8: Products with significant anogenital exposure |
| 0.051 % |
| Category 9: Products with body and hand exposure, primarily rinse off |
| 0.57 % |
| | Category 10: Household care products with mostly hand contact |
| Category 10A: Household care excluding aerosol products (excluding aerosol/spray products) |
| 0.57 % |
| Category 10B: Household aerosol/spray products |
| 4.20 % |
| | Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate |
| Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure |
| 0.051 % |
| Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure |
| 0.051 % |
| Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin |
| No Restriction |
| | Notes: |
| IFRA FLAVOR REQUIREMENTS: |
Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards. |
| |
| 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 |
| 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 |
| Click here to view publication 20 |
| | average usual ppm | average maximum ppm |
| baked goods: | 2.00000 | 10.00000 |
| beverages(nonalcoholic): | 0.10000 | 0.80000 |
| beverages(alcoholic): | 0.30000 | 2.00000 |
| breakfast cereal: | 0.10000 | 0.80000 |
| cheese: | - | - |
| chewing gum: | 2.00000 | 15.00000 |
| condiments / relishes: | - | - |
| confectionery froastings: | 0.30000 | 2.00000 |
| egg products: | 0.30000 | 2.00000 |
| fats / oils: | 0.30000 | 2.00000 |
| fish products: | - | - |
| frozen dairy: | 0.50000 | 6.00000 |
| fruit ices: | 0.20000 | 2.10000 |
| gelatins / puddings: | 0.20000 | 2.00000 |
| granulated sugar: | - | - |
| gravies: | 0.30000 | 2.00000 |
| hard candy: | 0.50000 | 5.00000 |
| imitation dairy: | - | - |
| instant coffee / tea: | 0.10000 | 1.00000 |
| jams / jellies: | 0.50000 | 5.00000 |
| meat products: | - | - |
| milk products: | 0.20000 | 2.10000 |
| nut products: | - | - |
| other grains: | - | - |
| poultry: | - | - |
| processed fruits: | - | - |
| processed vegetables: | - | - |
| reconstituted vegetables: | - | - |
| seasonings / flavors: | 0.50000 | 5.00000 |
| snack foods: | 0.50000 | 5.00000 |
| soft candy: | 0.50000 | 5.00000 |
| soups: | 0.10000 | 0.80000 |
| 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
|
Scientific Opinion on Flavouring Group Evaluation 72, Revision 2 (FGE.72Rev2): consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids and related esters evaluated by JECFA (61st, 68th and 69th meetings) and structurally related to flavouring substances in FGE.05Rev3
View page or View pdf
|
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations: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:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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]. |
|
