Tiglic acid methyl ester

Crotonic acid, ethyl ester. See Ethyl crotonate Crotonic acid, 2-methyl-, (E)-. See Tiglic acid Crotonic acid, methyl ester, (E)- (E)-Crotonic acid methyl ester. See Methyl crotonate Crotonic acid, 2-methyl-, ethyl ester, (E)-. See Ethyl tiglate... 

CAS 7785-33-3 EINECS/ELINCS 232-078-9 Synonyms 2-Butenoic acid, 2-methyl-, 3,7-dimethyl-2,6-octadienyl ester (E,E)- cis-a,p-Dimethyl acrylic acid, geraniol ester trans-3,7-Dimethyl-2,6-octadien-1-yl cis-a,p-dimethyl acrylate Geranyl trans-2-methyl-2-butenoate Tiglic acid, geraniol ester Empirical C15H24O2... 

CAS 61692-84-0 EINECS/ELINCS 262-908-5 Synonyms 2-Methylpropyl (E)-2-methyl-2-butenoate 2-Methylpropyl 2-methylcrotonate Tiglic acid isobutyl ester... 

Representatives of the subfamilies Omaliinae and Proteininae (omaliine group) possess an abdominal defensive gland reservoir that opens out between sternite 7 and 8 [ 120]. The multi-component mixtures contained in these glands are used for defence. In Omaliinae and Proteininae the secretion is characterized by mixtures of acids (e.g. 2-methylpropanoic acid, hexanoic acid, 2-octenoic acid, 2-methylbutanoic acid, 3-methylbutanoic acid, butyric acid, and tiglic acid), aldehydes (( )-2-hexenal, heptanal, octanal, nonanal), ketoaldehydes such as 4-oxo-2-hexenal 41 (Scheme 5), 6-methyl-5-hepten-2-one, alcohols (octanol, ( )-2-hexen-l-ol, 2-methylbutan-l-ol), alkanes (nonadecane), esters (2-methylbutyl tiglate 42, various propanoates, 2-hexenyl 3-methylbutanoate, 2-methylbutyl 2-methylbutanoate, octanoates,butanoates), and aromatic compounds (e.g. 2-phenethyl 3-methylbutanoate 43). Unusual compounds are 2-... 

Many mechanisms had been proposed in the past to rationalize this selectivity (tri-oxanes, perepoxide, exciplex, dipolar or biradical intermediates) however, it is now generally accepted that the reaction proceeds through an intermediate exciplex which has the structural requirements of a perepoxide. This assumption is supported by (a) the lack of stereoselectivity in the reactions with chiral oxazolines and tiglic acid esters (b) the comparison of the diastereoselectivity of dialkyl substituted acrylic esters with structurally similar non-functionalized aUtenes (c) the intermolecular isotope effects in the photooxygenation of methyl tiglate and (d) the solvent effects on regioselectivity. ... 

In nature, terpenoids are found to occur both in free and combined states. Most of the terpenoids that are not highly functionalized occur free. Carboxylic acids invariably occur in a free state, though occasional occurrence of methyl and other esters is known. Alcohols often occur both in the free state and as esters, in which the acid moiety is usually a simple aliphatic acid (e.g., acetic, tiglic, angelic, etc.) or less often an aromatic acid (e.g., benzoic, cinnamic), though esters... 

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