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9-Undecenoic acid, 11-[(2S,3R)-3-pentyl-2-oxiranyl]-, (9Z)- (Vernolic acid)

Delta notation: 12,13-O-18:1-delta-9c

Other Names: 9-Undecenoic acid, 11-(3-pentyloxiranyl)-, [2S-[2α(Z),3α]]-; 9-Undecenoic acid, 11-[(2S,3R)-3-pentyloxiranyl]-, (9Z)-; Oleic acid, 12,13-epoxy-, (12S,13R)-(+)-; Vernolic acid; (+)-12,13-Epoxy-9-cis-octadecenoic acid; (+)-Vernolic acid; Octadec-cis-(+)-12,13-epoxy-cis-9-enoic acid; Vernoleic acid; cis-(+)-12,13-Epoxyoctadec-cis-9-enoic acid

Formula: C18 H32 O3

Mass: 296.44

IUPAC name: (Z)-11-[(2S,3R)-3-pentyloxiran-2-yl]undec-9-enoic acid

9 undecenoic acid, 11 [(2s,3r) 3 pentyl 2 oxiranyl] , (9z)
Structure drawn at OPSIN (opsin.ch.cam.uk)

External Database IDs:
CAS registry: 503-07-1
SOFA Mol: M_329
Lipid Maps: LMFA02000282
PubChem: 6449780
ChEBI:

inchi: InChI=1/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m1/s1/f/h19H

stdinchi: InChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m1/s1

stdinchikey: CCPPLLJZDQAOHD-GJGKEFFFSA-N

smiles: C(CCCC)[C@@H]1[C@@H](O1)C\C=C/CCCCCCCC(=O)O

Results

Displaying datapoints 1 - 50 of 99 in total
Plant PublicationSort off ValueSort off UnitSort off
Abelmoschus esculentus AN OXYGENATED FATTY ACID FROM THE SEED OIL OF HIBISCUS ESCULENTUS Chisholm, M. J.; Hopkins, C. Y. Canadian Journal of Chemistry-Revue Canadienne De Chimie (1957) 35 358-364 3.0 GLC-Area-%
Albizia lebbeck Fatty acid profile ofAlbizia lebbeckandAlbizia samanseed oils: Presence of coronaric acid Knothe, Gerhard; Phoo, Zan Win Moh Moh; de Castro, Maria Ellenita G.; Razon, Luis F. European Journal of Lipid Science and Technology (2014) 117 567-574 0.2 weight-%
Albizia saman Fatty acid profile ofAlbizia lebbeckandAlbizia samanseed oils: Presence of coronaric acid Knothe, Gerhard; Phoo, Zan Win Moh Moh; de Castro, Maria Ellenita G.; Razon, Luis F. European Journal of Lipid Science and Technology (2014) 117 567-574 0.4 weight-%
Alchornea cordifolia Alchornea cordifolia seed oil: A rich source of a new C20 epoxide, (+)cis-14,15-epoxy-cis-11-eicosenoic acid Kleiman, R.; Plattner, R. D.; Spencer, G. F. Lipids (1977) 12 610-612 2.3 GLC-Area-%
Allium cernuum Unpublished unpublished results MRI (1997) 1.6 GLC-Area-%
Anthericum liliago Unpublished unpublished results MRI (1997) 2.3 GLC-Area-%
Arctium lappa Unpublished unpublished results MRI (1996) 2.5 GLC-Area-%
Artemisia absinthium EPOXY ACIDS OF OIL OF ARTEMISIA-ABSINTHIUM SEEDS Ulchenko, N. T.; Gigienova, E. I.; Umarov, A. U. Khimiya Prirodnykh Soedinenii (1976) None 705-710 1.48 GLC-Area-%
Bernardia pulchella The seed oil of Bernardia pulchella (Euphorbiaceae) - A rich source of vernolic acid Spitzer, V.; Aitzetmuller, K.; Vosmann, K. Journal of the American Oil Chemists Society (1996) 73 1733-1735 91.0 GLC-Area-%
Bombax costatum Physico-chemical properties of seed and fatty acid composition of Bombax costatum seed oil Ogbobe, O.; Ezeukwu, A. O.; Ozoh, N. G. Rivista Italiana delle Sostanze Grasse (1996) 73 271-272 13.0 GLC-Area-%
Carlina acaulis Unpublished unpublished results MRI Bundesforschungsanstalt Muenster (1996) 3.2 GLC-Area-%
Cassia siamea Cassia siamea seed oil: A minor source of vernolic and cyclopropenoid fatty acids Daulatabad, C. D.; Hosamani, K. M.; Mirajkar, A. M. Journal of the American Oil Chemists' Society (1988) 65 952-953 14.0 GLC-Area-%
Centratherum ritchiei CENTRATHERUM-RITCHIEI SEED OIL - CHARACTERIZATION OF VERNOLIC ACID Ahmad, R.; Ahmad, I.; Osman, S. M. Fett Wissenschaft Technologie-Fat Science Technology (1989) 91 488-490 30.1 GLC-Area-%
Cephalaria laevigata Unpublished unpublished results MRI Bundesforschungsanstalt Muenster (1994) 0.2 GLC-Area-%
Cephalaria transsylvanica Agronomic evaluation of prospective new crop species White, G. A.; Willingham, B. C.; Skrdla, W. H.; Massey, J. H.; Higgins, J. J.; Calhoun, W.; Davis, A. M.; Dolan, D. D.; Earle, F. R. Economic Botany (1971) 25 22-43 21.0 GLC-Area-%
Cephalaria setosa Screening for European productions of oilseed with unusual fatty acids Meier zu Beerentrup, H.; Robbelen, G. Angewandte Botanik (1987) 61 287-303 20.0 GLC-Area-%
Cephalaria setosa Agronomic evaluation of prospective new crop species White, G. A.; Willingham, B. C.; Skrdla, W. H.; Massey, J. H.; Higgins, J. J.; Calhoun, W.; Davis, A. M.; Dolan, D. D.; Earle, F. R. Economic Botany (1971) 25 22-43 25.0 GLC-Area-%
Cephalaria leucantha Identification and distribution of epoxyacyl groups in new, natural epoxy oils Tallent, W. H.; Cope, D. G.; Hagemann, J. W.; Earle, F. R.; Wolff, I. A. Lipids (1966) 1 335-340 27.0 GLC-Area-%
Cephalaria transsylvanica Unpublished unpublished results MRI Bundesforschungsanstalt Muenster (1995) 12.8 GLC-Area-%
Cephalaria leucantha Agronomic evaluation of prospective new crop species White, G. A.; Willingham, B. C.; Skrdla, W. H.; Massey, J. H.; Higgins, J. J.; Calhoun, W.; Davis, A. M.; Dolan, D. D.; Earle, F. R. Economic Botany (1971) 25 22-43 19.0 GLC-Area-%
Cephalocroton pueschelii Glyceride studies: Part IX: Intraglyceride distribution of vernolic acid and of five conjugated octadecatrienoic acids in seed glycerides Conacher, H. B. S.; Gunstone, F. D.; Hornby, G. M.; Padley, F. B. Lipids (1970) 5 434-441 72.0 GLC-Area-%
Citrullus sp. Unpublished results Aitzetmueller, K. et al. Unpublished (1997) 0.3 GLC-Area-%
Citrullus vulgaris Unpublished results Aitzetmueller, K. et al. Unpublished (1997) 0.8 GLC-Area-%
Clematis pubescens Unpublished results Aitzetmueller, K. et al. Unpublished (1997) 0.3 GLC-Area-%
Crepis aurea Agronomic evaluation of prospective new crop species White, G. A.; Willingham, B. C.; Skrdla, W. H.; Massey, J. H.; Higgins, J. J.; Calhoun, W.; Davis, A. M.; Dolan, D. D.; Earle, F. R. Economic Botany (1971) 25 22-43 54.0 GLC-Area-%
Crepis sibirica Unpublished unpublished results MRI (1995) 21.5 GLC-Area-%
Crepis capillaris Unpublished unpublished results MRI (1995) 48.9 GLC-Area-%
Crepis conyzaefolis EPOXYOCTADECADIENOIC ACIDS FROM CREPIS-CONYZAEFOLIA SEED OIL Spencer, G. F. Phytochemistry (1977) 16 282-284 32.0 GLC-Area-%
Crepis bungei Unpublished unpublished results MRI (1995) 8.9 GLC-Area-%
Crepis biennis Agronomic evaluation of prospective new crop species White, G. A.; Willingham, B. C.; Skrdla, W. H.; Massey, J. H.; Higgins, J. J.; Calhoun, W.; Davis, A. M.; Dolan, D. D.; Earle, F. R. Economic Botany (1971) 25 22-43 68.0 GLC-Area-%
Crescentia alata Morro seed oil Van Severen, M. L. Journal of the American Oil Chemists' Society (1960) 37 402-406 68.0 GLC-Area-%
Eremurus bungei Unpublished unpublished results MRI (1998) 0.3 GLC-Area-%
Erlangea tomentosa Glyceride structure of Erlangea tomentosa seed oil, a new source of vernolic acid Phillips, B. E.; Smith Jr, C. R.; Hagemann, J. W. Lipids (1969) 4 473-477 52.0 GLC-Area-%
Euphorbia lagascae Euphorbia lagascae Spreng., an abundant source of epoxyoleic acid; Seed extraction and oil composition Krewson, C. F.; Scott, W. E. Journal of the American Oil Chemists Society (1966) 43 171-174 63.7 GLC-Area-%
Euphorbia lagascae Search for new industrial oils. XII. Fifty-eight euphorbiaceae oils, including one rich in vernolic acid Kleiman, R.; Smith Jr, C. R.; Yates, S. G.; Jones, Q. Journal of the American Oil Chemists' Society (1965) 42 169-172 57.0 GLC-Area-%
Euphorbia lagascae FATTY-ACIDS IN PLANTS AND ANIMALS .2. TRANS UNSATURATED, ALKYNE, HYDROXY, EPOXY, OXO, CYCLOPROPANE AND CYCLOPROPENE FATTY-ACIDS Pohl, P.; Wagner, H. Fette Seifen Anstrichmittel Verbunden Mit Der Zeitschrift Die Ernahrungsindustrie (1972) 74 541-& 64.0 GLC-Area-%
Euphorbia lagascae FATTY-ACIDS IN PLANTS AND ANIMALS .2. TRANS UNSATURATED, ALKYNE, HYDROXY, EPOXY, OXO, CYCLOPROPANE AND CYCLOPROPENE FATTY-ACIDS Pohl, P.; Wagner, H. Fette Seifen Anstrichmittel Verbunden Mit Der Zeitschrift Die Ernahrungsindustrie (1972) 74 541-& 64.0 GLC-Area-%
Euphorbia lagascae Screening for European productions of oilseed with unusual fatty acids Meier zu Beerentrup, H.; Robbelen, G. Angewandte Botanik (1987) 61 287-303 60.2 GLC-Area-%
Euphorbia lagascae Unpublished Aitzetmueller, K. Unpublished Results (1992) 60.1 GLC-Area-%
Euphorbia lagascae FATTY-ACIDS IN PLANTS AND ANIMALS .2. TRANS UNSATURATED, ALKYNE, HYDROXY, EPOXY, OXO, CYCLOPROPANE AND CYCLOPROPENE FATTY-ACIDS Pohl, P.; Wagner, H. Fette Seifen Anstrichmittel Verbunden Mit Der Zeitschrift Die Ernahrungsindustrie (1972) 74 541-& 64.0 GLC-Area-%
Firmiana platanifolia Cyclopropene fatty acids of selected seed oils from bombacaceae, malvaceae, and sterculiaceae Bohannon, M. B.; Kleiman, R. Lipids (1978) 13 270-273 2.0 GLC-Area-%
Galeopsis bifida Unpublished unpublished results MRI (1996) 0.4 GLC-Area-%
Galeopsis speciosa New epoxy acids of Galeopsis bifida Asilbekova, D. T.; Gusakova, S. D.; Moiseeva, G. P.; Glushenkova, A. I. Chemistry of Natural Compounds (1987) 23 186-192 0.0 GLC-Area-%
Gentiana decumbens Unpublished unpublished results MRI (1996) 2.8 GLC-Area-%
Geranium sanguineum Unpublished Aitzetmueller, K. Tsevegsueren, N. unpublished results (1997) 8.4 GLC-Area-%
Geranium sanguineum Unpublished unpublished results MRI (1996) 7.1 GLC-Area-%
Geranium sanguineum Unpublished Aitzetmueller, K. unpublished results 5.2 GLC-Area-%
Geranium sanguineum Unpublished Aitzetmueller, K. unpublished results 7.1 GLC-Area-%
Geranium sanguineum Geranium sanguineum (Geraniaceae) seed oil: A new source of petroselinic and vernolic acid Tsevegsuren, N.; Aitzetmuller, K.; Vosmann, K. Lipids (2004) 39 571-576 6.9 weight-%
Geranium sanguineum Unpublished unpublished results MRI (1996) 5.2 GLC-Area-%