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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 ValueSort off Unit
Malva parviflora Cyclopropene fatty acids of selected seed oils from bombacaceae, malvaceae, and sterculiaceae Bohannon, M. B.; Kleiman, R. Lipids (1978) 13 270-273 7.0 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-%
Sigesbeckia orientalis 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-%
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-%
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-%
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-%
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 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-%
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-%
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 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 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-%
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-%
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-%
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-%
Geranium sanguineum Unpublished Aitzetmueller, K. Tsevegsueren, N. unpublished results (1997) 8.4 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-%
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-%
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-%
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-%
Allium cernuum Unpublished unpublished results MRI (1997) 1.6 GLC-Area-%
Piper nigrum Vernolic and Cyclopropenoic Fatty Acids in Piper nigrum Seed Oil Daulatabad, C. D.; Mulla, G. M.; Mirajkar, A. M. Lipid / Fett (1995) 97 453-454 7.7 GLC-Area-%
Crepis bungei Unpublished unpublished results MRI (1995) 8.9 GLC-Area-%
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-%
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-%
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-%
Crepis conyzaefolis EPOXYOCTADECADIENOIC ACIDS FROM CREPIS-CONYZAEFOLIA SEED OIL Spencer, G. F. Phytochemistry (1977) 16 282-284 32.0 GLC-Area-%
Malva parviflora Epoxy Acids and Epoxidized Oils I: Quantitative Evaluation of Naturally Occurring Epoxy Fatty Acids in Some Malvaceous seed Oils Hassan Mallah, M. M. El; Souka, L. M.; Gad, A. M. Fette, Seifen, Anstrichmittel (1966) 68 1028-1030 9.5 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-%
Vernonia sp. Referenz: (1957) 1-763 80.0 GLC-Area-%
Cephalaria laevigata Unpublished unpublished results MRI Bundesforschungsanstalt Muenster (1994) 0.2 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-%
Lagerstroemia thomsonii Vernolic acids from Lagerstroemia thomsonii and Bauhinia tomentosa seed oils Daulatabad, C. D.; Mulla, G. M.; Mirajkar, A. M. Journal of the Oil Technologists' Association of India (1991) 23 53-54 7.3 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-%
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-%
Gentiana decumbens Unpublished unpublished results MRI (1996) 2.8 GLC-Area-%
Geranium sanguineum Unpublished unpublished results MRI (1996) 7.1 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-%
Arctium lappa Unpublished unpublished results MRI (1996) 2.5 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-%
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-%
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-%
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-%
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-%
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-%
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