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trans,trans-2,4-Heptadienal

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trans,trans-2,4-Heptadienal Basic information

Product Name:
trans,trans-2,4-Heptadienal
Synonyms:
  • TRANS-2,TRANS-4-HEPTADIEN-1-AL
  • TRANS-2-TRANS-4-HEPTADIENAL
  • TRANS,TRANS-2,4-HEPTADIEN-1-AL
  • TRANS,TRANS-2,4-HEPTADIENAL
  • (2E,4E)-2,4-Heptadienal
  • (E)-2,(E)-4- heptadienal
  • (E,E)-2,4-Heptadien-1-al
  • (E,E)-2,4-Heptadienal
CAS:
4313-03-5
MF:
C7H10O
MW:
110.15
EINECS:
224-328-0
Product Categories:
  • Aldehydes
  • C7
  • API intermediates
  • aldehyde Flavor
  • Carbonyl Compounds
  • C7Volatiles/ Semivolatiles
  • E-L
  • Alpha Sort
Mol File:
4313-03-5.mol
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trans,trans-2,4-Heptadienal Chemical Properties

Melting point:
84.5 °C
Boiling point:
84-84.5 °C(lit.)
Density 
0.881 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.534(lit.)
FEMA 
3164 | (2E,4E)-HEPTADIENAL
Flash point:
150 °F
storage temp. 
2-8°C
solubility 
Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly)
form 
clear liquid
color 
Light yellow to Brown
Odor
at 1.00 % in dipropylene glycol. fatty green oily aldehydic vegetable cake cinnamon
Odor Type
fatty
Water Solubility 
INSOLUBLE
JECFA Number
1179
BRN 
1699244
Stability:
Light Sensitive
LogP
1.59
CAS DataBase Reference
4313-03-5(CAS DataBase Reference)
NIST Chemistry Reference
2,4-Heptadienal, (E,E)-(4313-03-5)
EPA Substance Registry System
2,4-Heptadienal, (2E,4E)- (4313-03-5)
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Safety Information

Hazard Codes 
T,Xi
Risk Statements 
22-24-38
Safety Statements 
36/37-45
RIDADR 
UN 2810 6.1/PG 3
WGK Germany 
3
10-23
Hazard Note 
Irritant
HazardClass 
6.1
PackingGroup 
III
HS Code 
29121900

MSDS

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trans,trans-2,4-Heptadienal Usage And Synthesis

Description

2,4-Heptadienal retards or prevents the development of "off-flavors" in auto-oxidizing fats and oils. May be prepared by reduction with LiAlH4 of the dienoic acid prepared by the Doebner synthesis, followed by oxidation with Mn02 of the resulting dienol to the corresponding dienol; by the method of Marshall and Whiting.

Chemical Properties

2,4-Heptadienal has a fatty, green odor In auto-oxidizing fats and oils, it retards or prevents the development of “off-favors ”.

Chemical Properties

clear yellow liquid

Occurrence

Reported found as a volatile component in boiled chicken, in peas by enzymatic formation from lipids, as the odorous component in Vaccinium macrocarpon; additional products in which 2,4-heptadienal has been reportedly identifed include soybean oil, black-tea aroma (trans- and cis-form); bilberry aroma (Vaccinium myrtillus); frozen peas, sunfower oil, autooxidized lard, salted salmon, sturgeon caviar and salmon roe; the trans,trans-form has been reported found among the volatile favor components of potato chips and tomato Also reported found in natural sources including cranberry, guava, melon, blackberry, avocado, cabbage, raw or cooked potato, tomato, butter, lean fsh, smoked fsh, chicken fat, cooked chicken, beef fat, tea, cooked beef, lamb and pork, peanut oil, peanut butter, mango, caulifower, broccoli, tamarind, fgs, corn tortillas, lemon balm, oysters, crayfsh, clams, mate and Virginia tobacco

Uses

trans,trans-2,4-Heptanedienal is an unsaturated aldehyde that has a fishy odour. trans,trans-2,4-Heptanedienal is a volatile component naturally found in drinking water and fish oils.

Definition

ChEBI: A heptadienal in which the two double bonds are located at positions 2 and 4 (the E,E-geoisomer).

Aroma threshold values

Aroma characteristics at 0.10%: green fatty, herbal, vegetative, aldehydic oily with cucumber and fried nuances.

Taste threshold values

Taste characteristics at 0.25 ppm: green fatty, harsh chicken fat, cucumber with brothy and fshy nuances.

General Description

2,4-Heptadienal is a specific marker of oxidative rancidity. It is also a potential algal metabolite.

Synthesis

By reduction with LiAlH4 of the dienoic acid prepared by the Doebner synthesis, followed by oxidation with MnO2 of the resulting dienol to the corresponding dienol; by the method of Marshall and Whiting.

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