111-79-5 Usage
Description
Methyl trans-2-nonenoate is a colorless to pale yellow liquid with a strong violet-leaf odor and a green, floral note. It is characterized by its violet-like scent and is soluble in alcohol. Methyl trans-2-nonenoate is not found in nature and is combustible.
Uses
Used in Perfumes:
Methyl trans-2-nonenoate is used as a fragrance ingredient in perfumes for its violet-like and green, floral notes. It imparts freshness to floral fragrance compositions and is recommended as a substitute for methyl 2-octynoate.
Used in Flavor Industry:
Methyl trans-2-nonenoate is used as a flavoring agent due to its taste threshold values, which give it a green, waxy, oily, fruity, watermelon rind, pearand apple-like taste at 5 ppm.
Preparation
Obtained in quantitative yields by treating methyl β-chlorocaproate with sodium acetate, or by dehydrogenating the corresponding saturated ester.
Synthesis Reference(s)
The Journal of Organic Chemistry, 54, p. 1831, 1989 DOI: 10.1021/jo00269a017Synthetic Communications, 24, p. 2069, 1994 DOI: 10.1080/00397919408010217Tetrahedron Letters, 30, p. 6555, 1989 DOI: 10.1016/S0040-4039(01)89020-1
Flammability and Explosibility
Notclassified
Trade name
Neofolione (Givaudan).
Metabolism
2-Nonenoic acid produced by the hydrolysis of methyl nonylenate will presumably pass through the normal pathways of fatty acid metabolism (Lehninger, 1970)
Check Digit Verification of cas no
The CAS Registry Mumber 111-79-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 111-79:
(5*1)+(4*1)+(3*1)+(2*7)+(1*9)=35
35 % 10 = 5
So 111-79-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O2/c1-3-4-5-6-7-8-9-10(11)12-2/h8-9H,3-7H2,1-2H3/b9-8+
111-79-5Relevant articles and documents
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Nakayama,M. et al.
, p. 184 - 185 (1979)
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Regioselective hydromethoxycarbonylation of terminal alkynes catalyzed by palladium(II)-tetraphos complexes
Oberhauser, Werner,Ienco, Andrea,Vizza, Francesco,Trettenbrein, Barbara,Oberhuber, Dennis,Strabler, Christof,Ortner, Teresa,Brueggeller, Peter
experimental part, p. 4832 - 4837 (2012/10/08)
An in situ generated dinuclear palladium hydride complex bearing cis,trans,cis-1,2,3,4-tetrakis(diphenylphosphanyl)cyclobutane catalyzed the hydromethoxycarbonylation of terminal alkynes, giving the corresponding branched α,β-unsaturated ester (A) with high regioselectivity.
Synthesis of α,α′-disubstituted linear ethers by an intermolecular nicholas reaction - Application to the synthesis of (+)-cis/-trans-lauthisan and (+)-cis/(+)-trans-obtusan
Ortega, Nuria,Martin, Tomas,Martin, Victor S.
scheme or table, p. 554 - 563 (2009/09/06)
A new and efficient methodology to prepare α,α'-disubstituted linear ethers through an intermolecular Nicholas reaction (interNR) is described. cis-2,8-Disubstituted oxocanes, cis-2,9-disubstituted oxonanes, their trans isomers, and their parent unsaturat