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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 51 - 99 of 99 in total
PlantSort off PublicationSort off Value UnitSort off
Pithecellobium dulce A minor source of vernolic, malvalic, and sterculic acids in Pithecollobium dulce (syn. Inga dulcis) seed oil Hosamani, K. M. Journal of the American Oil Chemists’ Society (1995) 72 489-492 10.0 GLC-Area-%
Quamoclit coccinea 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 10.2 GLC-Area-%
Lactuca sativa 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 10.5 GLC-Area-%
Lactuca sativa 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 10.5 GLC-Area-%
Cephalaria transsylvanica Unpublished unpublished results MRI Bundesforschungsanstalt Muenster (1995) 12.8 GLC-Area-%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-%
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-%
Malva parviflora Search for new industrial oils. VII Earle, F. R.; Wolff, I. A.; Glass, C. A.; Jones, Q. Journal of the American Oil Chemists Society (1962) 39 381-383 13.0 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-%
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-%
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-%
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 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-%
Crepis sibirica Unpublished unpublished results MRI (1995) 21.5 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-%
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-%
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-%
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-%
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-%
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-%
Crepis conyzaefolis EPOXYOCTADECADIENOIC ACIDS FROM CREPIS-CONYZAEFOLIA SEED OIL Spencer, G. F. Phytochemistry (1977) 16 282-284 32.0 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 sp. 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 40.0 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-%
Crepis capillaris Unpublished unpublished results MRI (1995) 48.9 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-%
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-%
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 Unpublished Aitzetmueller, K. Unpublished Results (1992) 60.1 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-%
Vernonia volkameriifolia Vernonia volkameriaefolia Seed oil: a rich source of epoxy acid Siddiqi, S. F.; Ahmad, F.; Siddiqi, M. S.; Osman, S. M.; Fenwick, G. R. Journal of the American Oil Chemists' Society (1984) 61 798-800 63.5 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 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 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-%
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-%
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-%
Vernonia pauciflora 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-%
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 anthelmintica Identification of peaks in gas-liquid chromatography Miwa, T. K. Journal of the American Oil Chemists' Society (1963) 40 309-313 74.0 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 STUDIES OF OILS OF UNUSUAL FATTY-ACIDS Raie, M. Y.; Zaka, S.; Khan, S.; Khan, S. A. Fette Seifen Anstrichmittel (1985) 87 324-326 76.8 GLC-Area-%
Vernonia afromontana Vernonia galamensis, Potential new crop source of epoxy acid Perdue, R. E.; Carlson, K. D.; Gilbert, M. G. Economic Botany (1986) 40 54-68 78.2 GLC-Area-%
Vernonia sp. Referenz: (1957) 1-763 80.0 GLC-Area-%
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-%
Vernonia lasiopus Vernonia galamensis, Potential new crop source of epoxy acid Perdue, R. E.; Carlson, K. D.; Gilbert, M. G. Economic Botany (1986) 40 54-68 81.3 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-%