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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
PlantSort off PublicationSort off ValueSort off Unit
Hibiscus furcatus CHEMICAL EXAMINATION OF THE HIBISCUS-FURCATUS SEED OIL Rao, C. S. C.; Nigam, S. S. Journal of the Indian Chemical Society (1979) 56 747-748 8.5
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-%
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-%
Thespesia populnea Identification of the Unsaturated Heptadecyl Fatty Acids in the Seed Oils of Thespesia populnea and Gossypium hirsutum Dowd, Michael K. Journal of the American Oil Chemists' Society (2012) 89 1599-1609 0.11 weight-%
Gossypium hirsutum Identification of the Unsaturated Heptadecyl Fatty Acids in the Seed Oils of Thespesia populnea and Gossypium hirsutum Dowd, Michael K. Journal of the American Oil Chemists' Society (2012) 89 1599-1609 3.03 weight-%
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-%
Vernonia galamensis Triacylglycerols of Vernonia galamensis seed oil Ncube, I.; Read, J. S.; Adlercreutz, P.; Mattiasson, B. Phytochemistry (1998) 47 723-727 80.0 GLC-Area-%
Geranium sanguineum Unpublished Aitzetmueller, K. unpublished results 7.1 GLC-Area-%
Geranium sanguineum Unpublished Aitzetmueller, K. unpublished results 5.2 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-%
Rivea ornata Industrial utilization of Rivea ornata seed oil: A moderate source of vernolic acid Hosamani, K. M.; Sattigeri, R. M. Industrial Crops and Products (2000) 12 93-96 22.0 GLC-Area-%
Syzygium cumini EPOXY AND CYCLOPROPENOID FATTY-ACIDS IN SYZYGIUM-CUMINII SEED OIL Daulatabad, Cmjd; Mirajkar, A. M.; Hosamani, K. M.; Mulla, G. M. M. Journal of the Science of Food and Agriculture (1988) 43 91-94 3.0 GLC-Area-%
Hibiscus mutabilis HIBISCUS MUTABILIS SEED OIL - CHARACTERIZATION OF HBR-REACTIVE ACIDS Husain, S. R.; Ahmad, M. S.; Ahmad, F.; Ahmad, M.; Osman, S. M. Fett Wissenschaft Technologie-Fat Science Technology (1989) 91 167-168 5.9 GLC-Area-%
Mucuna prurita EPOXY ACIDS OF MUCUNA-PRURITA SEED OIL Hasan, S. Q.; Sherwani, M. R. K.; Ahmad, I.; Ahmad, F.; Osman, S. M. Journal of the Indian Chemical Society (1980) 57 920-923 4.0 GLC-Area-%
Quamoclit phoenicea Epoxy oleic acid in Quamoclit seed oils Daulatabad, C. D.; Desai, V. A.; Hosamani, K. M.; Hiremath, V. B. Journal of the American Oil Chemists' Society (1992) 69 190-191 6.4 GLC-Area-%
Crepis sibirica Unpublished unpublished results MRI (1995) 21.5 GLC-Area-%
Crepis capillaris Unpublished unpublished results MRI (1995) 48.9 GLC-Area-%
Salmalia malabarica Cyclopropene fatty acids of selected seed oils from bombacaceae, malvaceae, and sterculiaceae Bohannon, M. B.; Kleiman, R. Lipids (1978) 13 270-273 1.0 GLC-Area-%
Hibiscus sabdariffa FA and tocopherol composition of Vietnamese oilseeds Matthaus, Bertrand; Vosmann, Klaus; Pham, Long Quoc; Aitzetmüller, Kurt Journal of the American Oil Chemists' Society (2003) 80 1013-1020 2.7 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-%
Citrullus sp. Unpublished results Aitzetmueller, K. et al. Unpublished (1997) 0.3 GLC-Area-%
Clematis pubescens Unpublished results Aitzetmueller, K. et al. Unpublished (1997) 0.3 GLC-Area-%
Galeopsis bifida Unpublished unpublished results MRI (1996) 0.4 GLC-Area-%
Lactuca scariola COOCCURRENCE OF CORONARIC AND VERNOLIC ACIDS IN COMPOSITAE SEED OILS Ansari, M. H.; Ahmad, S.; Ahmad, F.; Ahmad, M.; Osman, S. M. Fett Wissenschaft Technologie-Fat Science Technology (1987) 89 116-118 4.0 GLC-Area-%
Carlina acaulis Unpublished unpublished results MRI Bundesforschungsanstalt Muenster (1996) 3.2 GLC-Area-%
Gyrocarpus americanus Unpublished unpublished results MRI (1997) 3.3 GLC-Area-%
Plectranthus mollis Vernolic and Cyclopropenoid Fatty Acids in Plectranthus mollis Syn. Plenctranthus incanus, Link, Seed Oil: A Rich Source of Oil Daulatabad, C.D. et al. Abstr. Nr. 39 In: J. Oil Technol. Assoc. India (1988) 20 128 6.1 GLC-Area-%
Citrullus vulgaris Unpublished results Aitzetmueller, K. et al. Unpublished (1997) 0.8 GLC-Area-%
Eremurus bungei Unpublished unpublished results MRI (1998) 0.3 GLC-Area-%
Kigelia pinnata KIGELIA PINNATA SEED OIL - A MODERATE SOURCE OF VERNOLIC ACID Afaque, S.; Siddiqui, M. M.; Ahmad, I.; Siddiqui, M. S.; Osman, S. M. Fett Wissenschaft Technologie-Fat Science Technology (1987) 89 433-435 22.3 GLC-Area-%
Vernonia anthelmintica Vernonia anthelmintica (L.) Willd. trivernolin, 1,3-divernolin and vernolic (Epoxyoleic) acid from the seed oil Krewson, C. F.; Ard, J. S.; Riemenschneider, R. W. Journal of the American Oil Chemists Society (1962) 39 334-340 75.0 GLC-Area-%
Vernonia anthelmintica Analysis of lipids containing epoxy groups: The epoxy glycerides of Vernonia anthelmintica seed oil Fioriti, J. A.; Buide, N.; Sims, R. J. Journal of the American Oil Chemists' Society (1969) 46 108-112 31.4 GLC-Area-%
Vernonia cinerea VEGETABLE OILS .11. COMPONENT ACIDS OF TORRESEA CEARENSIS SEED OIL Badami, R. C.; Gunstone, F. D. Journal of the Science of Food and Agriculture (1963) 14 479-& 28.0 GLC-Area-%
Vernonia colorata VEGETABLE OILS .11. COMPONENT ACIDS OF TORRESEA CEARENSIS SEED OIL Badami, R. C.; Gunstone, F. D. Journal of the Science of Food and Agriculture (1963) 14 479-& 38.0 GLC-Area-%
Vernonia hymenolepis 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 65.0 GLC-Area-%
Vernonia nigritiana VEGETABLE OILS .11. COMPONENT ACIDS OF TORRESEA CEARENSIS SEED OIL Badami, R. C.; Gunstone, F. D. Journal of the Science of Food and Agriculture (1963) 14 479-& 8.0 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 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 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-%
Vernonia adoensis 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 43.0 GLC-Area-%
Leonurus sibiricus Leonurus sibiricus oil: a new and rich source of epoxy and palmitoleic acids Mukarram, M.; Ahmad, M. Journal of the Oil Technologists' Association of India (Mumbai, India) (1983) 15 14-15 13.0 GLC-Area-%
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-%
Sonchus oleraceus SONCHUS OLERACEUS SEED OIL - CHARACTERIZATION OF HBR-REACTIVE OXYGENATED ACID Ahmad, R.; Ahmad, I.; Ahmad, F.; Osman, S. M. Fette Seifen Anstrichmittel (1986) 88 490-492 13.7 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-%
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-%
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-%
Geranium sanguineum Unpublished unpublished results MRI (1996) 5.2 GLC-Area-%
Geranium sanguineum Unpublished unpublished results MRI (1996) 8.4 GLC-Area-%
Malope trifida Cyclopropene fatty acids of selected seed oils from bombacaceae, malvaceae, and sterculiaceae Bohannon, M. B.; Kleiman, R. Lipids (1978) 13 270-273 6.5 GLC-Area-%