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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 Value UnitSort off
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-%
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-%
Cephalaria laevigata Unpublished unpublished results MRI Bundesforschungsanstalt Muenster (1994) 0.2 GLC-Area-%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-%
Clematis pubescens Unpublished results Aitzetmueller, K. et al. Unpublished (1997) 0.3 GLC-Area-%
Eremurus bungei Unpublished unpublished results MRI (1998) 0.3 GLC-Area-%
Citrullus sp. Unpublished results Aitzetmueller, K. et al. Unpublished (1997) 0.3 GLC-Area-%
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-%
Galeopsis bifida Unpublished unpublished results MRI (1996) 0.4 GLC-Area-%
Citrullus vulgaris Unpublished results Aitzetmueller, K. et al. Unpublished (1997) 0.8 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-%
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-%
Allium cernuum Unpublished unpublished results MRI (1997) 1.6 GLC-Area-%
Leucas martinicensis Leucas martinicensis: potential new semi-arid crop source of industrial oil Ogbobe, O. Rivista Italiana delle Sostanze Grasse (1992) 69 285-286 1.7 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-%
Anthericum liliago Unpublished unpublished results MRI (1997) 2.3 GLC-Area-%
Arctium lappa Unpublished unpublished results MRI (1996) 2.5 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-%
Gentiana decumbens Unpublished unpublished results MRI (1996) 2.8 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-%
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-%
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-%
Carlina acaulis Unpublished unpublished results MRI Bundesforschungsanstalt Muenster (1996) 3.2 GLC-Area-%
Gyrocarpus americanus Unpublished unpublished results MRI (1997) 3.3 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-%
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-%
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-%
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-%
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-%
Hibiscus sabdariffa HIBISCUS-SABDARIFFA SEED OIL - REINVESTIGATION Ahmad, M. U.; Husain, S. K.; Ahmad, I.; Osman, S. M. Journal of the Science of Food and Agriculture (1979) 30 424-428 4.5 GLC-Area-%
Geranium sanguineum Unpublished unpublished results MRI (1996) 5.2 GLC-Area-%
Geranium sanguineum Unpublished Aitzetmueller, K. unpublished results 5.2 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-%
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-%
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-%
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-%
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-%
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-%
Geranium sanguineum Unpublished unpublished results MRI (1996) 7.1 GLC-Area-%
Geranium sanguineum Unpublished Aitzetmueller, K. unpublished results 7.1 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-%
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-%
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-%
Geranium sanguineum Unpublished unpublished results MRI (1996) 8.4 GLC-Area-%
Geranium sanguineum Unpublished Aitzetmueller, K. Tsevegsueren, N. unpublished results (1997) 8.4 GLC-Area-%
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
Crepis bungei Unpublished unpublished results MRI (1995) 8.9 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-%
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-%