2,4-Decadienal
Basic information
- CAS
2363-88-4- Standard SMILES
CCCCC/C=C/C=C/C=O- InChIKey
JZQKTMZYLHNFPL-BLHCBFLLSA-N- Molecular formula
- C10H16O
- Average molar mass
- 152.23 g/mol
- Monoisotopic mass
- 152.12011513
Overview
(2E,4E)-deca-2,4-dienal is a polyunsaturated fatty aldehyde that is decanal which has undergone formal dehydrogenation to introduce trans- double bonds at the 2-3 and 4-5 positions. A product of lipid peroxidation in cell membranes and a component of cooking oil fumes. It has a role as a nematicide and an apoptosis inducer.
Names & identifiers
- Preferred name
- 2,4-Decadienal
- IUPAC
- (2E,4E)-deca-2,4-dienal
- English name
- trans,trans-2,4-Decadienal
- Molecular formula
- C10H16O
- Molecular weight
- 152.23
Names & synonyms
2,4-DECADIENAL2363-88-4DTXSID4047626RefChem:908722DTXCID2027626219-114-9(2E,4E)-deca-2,4-dienaltrans,trans-2,4-Decadienal25152-84-5(E,E)-2,4-Decadienal2,4-Decadienal, (2E,4E)-trans,trans-2,4-Decadien-1-al
Show more names
DDAFEMA 3135TRANS-2, TRANS-4-DECADIENALDECA-2,4-DIENAL2,4-DECADIEN-1-AL4-DECADIENALDECADIENAL 2,42E,4E-DECADIENALT2 T4 DECADIENAL
(2E,4E)-Decadienal2,4-Decadienal, (E,E)-(2E,4E)-2,4-Decadienal2-trans-4-trans-Decadienal2,4,7-tridecadienalMFCD00007007FEMA No. 31352-trans,4-trans-decadienal
Database identifiers
- CAS
2363-88-4、25152-84-5、30551-18-9- PubChem CID
- 5283349
- DTXSID
DTXSID6024911- ChEMBL
CHEMBL443949- ChEBI
CHEBI:149547- UNII
- 3G88X2RK09
- EC Number
- 219-114-9、246-668-9
- Nikkaji
- J80.457F、J88.326C
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 6
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 134
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Aldehydes
LipidsFatty Acyls [FA] -> Fatty aldehydes [FA06]
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.866-0.876
Flavoring AgentsEU Flavoring substances
Solubility
soluble in fixed oils; Insoluble in water
soluble (in ethanol)
Boiling Point104 °C
Refractive Index1.512-1.517
Physical Description
Pale yellow to dark brown liquid with a buttery, fatty, orange odor; [Advanced BioTech MSDS] Strong green odor; Odor like sweet oranges at high concentrations; [Citrus and Allied Essences MSDS]
Yellow liquid; powerful, oily, like chicken fat
Physicochemical properties
- Boiling point
- 114 · 114-116 °C10 mm Hg(lit.)
- Density
- 0.872 g/mL · 0.872 g/mL at 20 °C(lit.)
- vapor density
- 1 · >1 (vs air)
- FEMA
- 3135 · 3135 | 2-TRANS,4-TRANS-DECADIENAL
- refractive index
- 20 · n20/D 1.515(lit.)
- FLAVIS Number
- 5.081 · 05.081 | 2,4-Decadienal
- Flash point
- 214 °F · 214 °F
- storage temp.
- -20 °C · Amber Vial, -20°C Freezer, Under Inert Atmosphere
- solubility
- Chloroform (Slightly), DMSO (Sparingly), Ethyl Acetate, Methanol
- form
- Oil
- color
- Pale Yellow to Yellow
- Odor
- 1 % · at 1.00 % in dipropylene glycol. orange sweet fresh citrus fatty green
- Odor Type
- fatty
- Stability
- Light Sensitive
- Cosmetics Ingredients Functions
- PERFUMING
- LogP
- 3.419 · 3.419 (est)
- CAS DataBase Reference
- 2363 · 2363-88-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 3 G88X2RK09 · 3G88X2RK09
- EPA Substance Registry System
- 2 · 2,4-Decadienal (2363-88-4)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 312 · H312-H315-H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362-P280-P302+P352-P312-P322-P363-P501
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 2 · 2
- RTECS
- 3000000 · HD3000000
- F
- 10 · 10-23
- TSCA
- TSCA listed
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H312 (99.9%): Harmful in contact with skin [Warning Acute toxicity, dermal]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P317, P321, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1607 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
This chemical does not meet GHS hazard criteria for 0.4% (1 of 253) of reports.
Warning
Hazard information
Regulatory Information
Chemical: 2,4-Decadienal
Chemical: 2,4-Decadienal, (E,E)-
Regulation (EC) No 1831/2003 (amended)
2,4-Decadienal: Does not have an individual approval but may be used under an appropriate group standard
2,4-Decadienal, (2E,4E)-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryAn irritant; [Advanced BioTech MSDS] A skin irritant in rabbits; Undiluted product may cause eye irritation; At 2% in petroleum causes no skin irritation or sensitization in humans; [Bedoukian Research MSDS] See 2,4-Hexadienal.
Hazard Classes and Categories
Acute Tox. 4 (81%)
Acute Tox. 4 (99.9%)
Safety data
- F
- 10-23
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- HD3000000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Hazard statements
- H312-H315-H319
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362-P280-P302+P352-P312-P322-P363-P501
Chemistry & industry
Uses & manufacturing
UsesUsed as flavoring agent; [Advanced BioTech MSDS]
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information
2,4-Decadienal: ACTIVE
2,4-Decadienal, (2E,4E)-: ACTIVE
Applications
OccurrenceReported as occurring in peanut oil and, as a volatile component, in fried potatoes, the trans, trans- form is reported found among the volatile flavor components of potato chips and tomato. Also found in citrus peel oils, orange juice, tangerine juice, guava fruit, strawberry fruit, cabbage, carrot, raw potato, bell pepper, butter, cooked chicken, beer, rum, tea, peanut oil, popcorn, potato chips, corn tortilla, oatmeal, Brazil nut, roasted almonds, roasted peanuts and pecans, soybeans, cassava, caviar, cooked beef, lamb, mutton, and fish.
Usestrans,trans-2,4-Decadienal is an aldehyde with a fat flavor aroma characteristic of chicken but has a citrus odor at lower concentrations. trans,trans-2,4-Decadienal can be found in butter, cooked beef, fish, potato chips, roasted peanut, buckwheat and wheat bread crumb.
Preparation methods
PreparationBy autooxidation of methyl (trans, trans)-linolate hydroperoxide.
Additional notes
DefinitionChEBI: (2E,4E)-deca-2,4-dienal is a polyunsaturated fatty aldehyde that is decanal which has undergone formal dehydrogenation to introduce trans- double bonds at the 2-3 and 4-5 positions. A product of lipid peroxidation in cell membranes and a component of cooking oil fumes. It has a role as a nematicide and an apoptosis inducer.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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