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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
Plant PublicationSort off ValueSort off UnitSort off
Geranium sanguineum Unpublished unpublished results MRI (1996) 8.4 GLC-Area-%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-%
Gyrocarpus americanus Unpublished unpublished results MRI (1997) 3.3 GLC-Area-%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-%
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-%
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-%
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
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-%
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 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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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-%
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 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 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-%
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-%
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-%
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 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 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 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 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 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 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 sp. Referenz: (1957) 1-763 80.0 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-%