111-79-5 Usage
Description
Methyl 2-nonenoate has a characteristic violet-like odor. May be
obtained in quantitative yields by treating methyl P-chlorocaproate
with sodium acetate, or by dehydrogenating the corresponding
saturated ester.
Physical properties
Methyl trans-2-nonenoate is colorless to slightly yellow liquid;strong violet-leaf odor. Stable; soluble in alco-hol. Combustible.
Chemical Properties
Methyl 2-Nonenoate is a colorless to pale yellow liquid
with a green, floral note. It imparts freshness to floral fragrance compositions
and is recommended as a substitute for methyl 2-octynoate.The synthesis consists
of a condensation of heptanal withmalonic acid, decarboxylation, and subsequent
esterification with methanol.
Occurrence
Methyl trans-2-nonenoate has apparently not been reported to occur in nature.
Uses
Perfumes.
Preparation
Obtained in quantitative yields by treating methyl β-chlorocaproate with sodium acetate, or by dehydrogenating the corresponding saturated ester.
Taste threshold values
Taste characteristics at 5 ppm: green, waxy, oily, fruity, watermelon rind, pear- and apple-like.
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
