4313-03-5 Usage
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
Different sources of media describe the Chemical Properties of 4313-03-5 differently. You can refer to the following data:
1. 2,4-Heptadienal has a fatty, green odor In auto-oxidizing fats and oils, it retards or prevents the development of “off-favors ”.
2. 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
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.
Check Digit Verification of cas no
The CAS Registry Mumber 4313-03-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,3,1 and 3 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4313-03:
(6*4)+(5*3)+(4*1)+(3*3)+(2*0)+(1*3)=55
55 % 10 = 5
So 4313-03-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H10O/c1-2-3-4-5-6-7-8/h3-7H,2H2,1H3/b4-3-,6-5-
4313-03-5Relevant articles and documents
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Nishida,S.,Kataoka,F.
, p. 1297 - 1298 (1976)
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Iron-catalyzed aerobic oxidation of allylic alcohols: The issue of C=C bond isomerization
Liu, Jinxian,Ma, Shengming
supporting information, p. 5150 - 5153 (2013/11/06)
An aerobic oxidation of allylic alcohols using Fe(NO3) 3·9H2O/TEMPO/NaCl as catalysts under atmospheric pressure of oxygen at room temperature was developed. This eco-friendly and mild protocol provides a convenient pathway to the synthesis of stereodefined α,β-unsaturated enals or enones with the retention of the C-C double-bond configuration.
Straightforward preparation of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal
Petroski, Richard J.
, p. 3233 - 3241 (2007/10/03)
A concise synthesis of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal is presented. Commercially available (Z)-2-penten-1-ol was converted to ethyl-(2E,4Z)-2,4-heptadienoate by reaction with activated MnO2 and (carboethoxymethylene)triphenylphosphorane in the presence of benzoic acid as a catalyst. Ethyl-(2E,4Z)-2,4-hep-tadienoate was converted to (2E,4Z)-2,4-heptadien-1-ol with LiAlH4. The alcohol was partially oxidized to (2E,4Z)-2,4-heptadienal with MnO2. The title compounds are male-specific, antennally active volatile compounds from the Saltcedar leaf beetle, Diorhabda elongata Brulle (Coleoptera: Chrysomelidae) and have potential use in the biological control of the invasive weed saltcedar (Tamarix spp).
