petroselinic acid
6-octadecenoic acid
 
Notes:
Isol. from volatiles of Coriandrum sativum (coriander), Anethum sowa (Indian dill), Cuminum cyminum (cumin), Daucus carota (carrot), Nigella sativa (black cumin), Apium graveolens (celery), Pimpinella anisum (anise) and Petroselinum sativum (parsley) [CCD] Found in umbelliferous seed oils e.g. major constit. of oils of parsley, ivy, fennel, celery and others [DFC] Minor constit. of plant oils. Constit. of milk fat and from porcine parasites Oesophagostomum dentatum and Oesophagostomum quadrispinulatum [CCD]
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CAS Number: 593-40-8Picture of molecule3D/inchi
XlogP3-AA: 7.30 (est)
Molecular Weight: 282.46738000
Formula: C18 H34 O2
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 399.00 to  400.00 °C. @ 760.00 mm Hg (est)
Flash Point: 564.00 °F. TCC ( 295.80 °C. ) (est)
logP (o/w): 7.481 (est)
Soluble in:
 alcohol
 water, 0.01151 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
ExtraSynthese
For experimental / research use only.
Petroselinic Acid
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for petroselinic acid usage levels up to:
 not for fragrance use.
 
Recommendation for petroselinic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 11634
National Institute of Allergy and Infectious Diseases: Data
 octadec-6-enoic acid
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References:
 octadec-6-enoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 11634
Pubchem (sid): 85088540
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
KEGG (GenomeNet): C08363
HMDB (The Human Metabolome Database): HMDB02080
FooDB: FDB012765
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 anise seed
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 caraway plant
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 caraway seed
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 caraway seed oil
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 carrot seed
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 celery seed
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 celery seed oil
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 chervil seed
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 coriander fruit
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 coriander seed
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 coriander seed oil
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 cumin seed
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 cumin seed oil
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 dill plant
Search Trop  Picture
 dill seed
Search Trop  Picture
 fennel absolute @ 5.80%
Data  GC  Search Trop  Picture
 fennel seed
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 fennel seed oil
Search Trop  Picture
 melon bitter melon seed oil
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 parsley
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 parsley fruit
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 parsley seed
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 parsley seed oil
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 parsnip seed
Search Trop  Picture
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Synonyms:
 octadec-6-enoic acid
6-octadecenoic acid
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Articles:
PubMed: Evaluation of coriander spice as a functional food by using in vitro bioassays.
PubMed: Fatty Acid Composition and Volatile Constituents of Protaetia brevitarsis Larvae.
PubMed: Effects of dietary supplementation of coriander oil, in canola oil diets, on the metabolism of [1-(14)C] 18:3n-3 and [1-(14)C] 18:2n-6 in rainbow trout hepatocytes.
PubMed: Evaluation of the impact of dietary petroselinic acid on the growth performance, fatty acid composition, and efficacy of long chain-polyunsaturated fatty acid biosynthesis of farmed Nile tilapia.
PubMed: Gas chromatography-mass spectrometry analysis on compounds in volatile oils extracted from yuan zhi (radix polygalae) and shi chang pu (acorus tatarinowii) by supercritical CO2.
PubMed: Coriander (Coriandrum sativum L.): a potential source of high-value components for functional foods and nutraceuticals--a review.
PubMed: Identification of Δ6-monounsaturated fatty acids in human hair and nail samples by gas-chromatography-mass-spectrometry using ionic-liquid coated capillary column.
PubMed: Essential oils and fatty acids composition of Tunisian and Indian cumin (Cuminum cyminum L.) seeds: a comparative study.
PubMed: Specific unsaturated fatty acids enforce the transdifferentiation of human cancer cells toward adipocyte-like cells.
PubMed: Resolution and quantification of isomeric fatty acids by silver ion HPLC: fatty acid composition of aniseed oil (Pimpinella anisum, Apiaceae).
PubMed: Sulfonic-hydroxyl-type heterogemini surfactants synthesized from unsaturated fatty acids.
PubMed: Fatty acid and essential oil composition of three Tunisian caraway (Carum carvi L.) seed ecotypes.
PubMed: Using a novel petroselinic Acid embedded cellulose acetate membrane to mimic plant partitioning and in vivo uptake of polycyclic aromatic hydrocarbons.
PubMed: Substrate selectivity of 5-hydroxyeicosanoid dehydrogenase and its inhibition by 5-hydroxy-Delta6-long-chain fatty acids.
PubMed: Infrared spectroscopy and differential scanning calorimetry studies of binary combinations of cis-6-octadecenoic acid and octadecanoic acid.
PubMed: Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification.
PubMed: Genomic structures and characterization of the 5'-flanking regions of acyl carrier protein and Delta4-palmitoyl-ACP desaturase genes from Coriandrum sativum.
PubMed: A multifunctional acyl-acyl carrier protein desaturase from Hedera helix L. (English ivy) can synthesize 16- and 18-carbon monoene and diene products.
PubMed: Geranium sanguineum (Geraniaceae) seed oil: a new source of petroselinic and vernolic acid.
PubMed: [2,4-Dienoyl-CoA reductases: from discovery toward pathophysiological significance].
PubMed: Quantitative 2H NMR analysis of deuterium distribution in petroselinic acid isolated from parsley seed.
PubMed: What limits production of unusual monoenoic fatty acids in transgenic plants?
PubMed: Base-catalyzed derivatization methodology for FA analysis. application to milk fat and celery seed lipid TAG.
PubMed: Novel methoxylated FA from the Caribbean sponge Spheciospongia cuspidifera.
PubMed: Dibutyrate derivatization of monoacylglycerols for the resolution of regioisomers of oleic, petroselinic, and cis-vaccenic acids.
PubMed: An unusual seed-specific 3-ketoacyl-ACP synthase associated with the biosynthesis of petroselinic acid in coriander.
PubMed: The genus Thapsia as a source of petroselinic acid.
PubMed: Inhibition of topoisomerases by fatty acids.
PubMed: Function of human mitochondrial 2,4-dienoyl-CoA reductase and rat monofunctional Delta3-Delta2-enoyl-CoA isomerase in beta-oxidation of unsaturated fatty acids.
PubMed: Adipose tissue triacylglycerols of rats are modulated differently by dietary isomeric octadecenoic acids from coriander oil and high oleic sunflower oil.
PubMed: Alternatives to the isomerase-dependent pathway for the beta-oxidation of oleic acid are dispensable in Saccharomyces cerevisiae. Identification of YOR180c/DCI1 encoding peroxisomal delta(3,5)-delta(2,4)-dienoyl-CoA isomerase.
PubMed: Sources of NADPH and expression of mammalian NADP+-specific isocitrate dehydrogenases in Saccharomyces cerevisiae.
PubMed: Skin penetration enhancing action of cis-unsaturated fatty acids with omega-9, and omega-12-chain lengths.
PubMed: Peroxisomal beta-oxidation of polyunsaturated fatty acids in Saccharomyces cerevisiae: isocitrate dehydrogenase provides NADPH for reduction of double bonds at even positions.
PubMed: Identification of the novel 7-methyl-6-octadecenoic acid in Holothuria mexicana.
PubMed: Fat infiltration in liver of rats induced by different dietary plant oils: high oleic-, medium oleic- and high petroselinic acid-oils.
PubMed: Isolation and characterization of a delta-9 fatty acid desaturase gene from the oleaginous yeast Cryptococcus curvatus CBS 570.
PubMed: Petroselinic acid from dietary triacylglycerols reduces the concentration of arachidonic acid in tissue lipids of rats.
PubMed: Transactivation by PPAR/RXR heterodimers in yeast is potentiated by exogenous fatty acid via a pathway requiring intact peroxisomes.
PubMed: Apparent Role of Phosphatidylcholine in the Metabolism of Petroselinic Acid in Developing Umbelliferae Endosperm.
PubMed: Specificities of the Acyl-Acyl Carrier Protein (ACP) Thioesterase and Glycerol-3-Phosphate Acyltransferase for Octadecenoyl-ACP Isomers (Identification of a Petroselinoyl-ACP Thioesterase in Umbelliferae).
PubMed: Metabolic Evidence for the Involvement of a [delta]4-Palmitoyl-Acyl Carrier Protein Desaturase in Petroselinic Acid Synthesis in Coriander Endosperm and Transgenic Tobacco Cells.
PubMed: Petroselinic acid biosynthesis and production in transgenic plants.
PubMed: Heteronuclear NMR analysis of unsaturated fatty acids in poly(3-hydroxyalkanoates). Study of beta-oxidation in Pseudomonas putida.
PubMed: Expression of a coriander desaturase results in petroselinic acid production in transgenic tobacco.
PubMed: [Chemical and biological properties of coriander fatty oil].
PubMed: Lipase from Brassica napus L. discriminates against cis-4 and cis-6 unsaturated fatty acids and secondary and tertiary alcohols.
PubMed: Evidence for the essential function of 2,4-dienoyl-coenzyme A reductase in the beta-oxidation of unsaturated fatty acids in vivo. Isolation and characterization of an Escherichia coli mutant with a defective 2,4-dienoyl-coenzyme A reductase.
PubMed: Isolation and characterization of a novel four-chain ether lipid from Clostridium butyricum: the phosphatidylglycerol acetal of plasmenylethanolamine.
PubMed: Lipid shape as a determinant of lipid composition in Clostridium butyricum. The effects of incorporation of various fatty acids on the ratios of the major ether lipids.
PubMed: Incorporation of cis-octadecenoic acids into the rat liver mitochondrial membrane phospholipids and adipose tissue triglycerides.
PubMed: Unusual fatty acids in the lipids from organs and cell cultures ofPetroselinum crispum.
PubMed: Effect of fatty acids on growth of Japanese encephalitis virus cultivated in BHK-21 cells and phospholipid metabolism of the infected cells.
PubMed: Temperature-dependent changes in activation energies of the transport systems for nucleosides, choline and deoxyglucose of cultured Novikoff rat hepatoma cells and effects of cytochalasin B and lipid solvents.
PubMed: Studies on the specificity of a lipase system fromGeotrichum candidum.
PubMed: Determination of petroselinic acid by microreactor chromatography.
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