(Z)-oleic acid

(Z)-9-octadecenoic acid

CAS: 112-80-1 C18 H34 O2 MW: 282.46738000 fatty fatty

Identification

Name(Z)-oleic acid
IUPAC(Z)-octadec-9-enoic acid
CAS Number112-80-1
EINECS204-007-1
FDA UNII2UMI9U37CP
Molecular FormulaC18 H34 O2
Molecular Weight282.46738000
MDL NumberMFCD00064242
Nikkaji NumberJ2.460K
Beilstein1726542
CoE Number13
XlogP36.50 (est)

Regulatory

FDA/DG SANTE Petitions, Reviews, Notices1975
JECFA Food Flavoring333 (Z)-oleic acid
DG SANTE Food Flavourings08.013 oleic acid
DG SANTE Food Contact Materialsoleic acid
FEMA Number2815
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)112-80-1 ; OLEIC ACID
FDA RegulationFDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION

Physical Properties

Appearance colorless to pale yellow liquid (est)
Food Chemicals Codex Listed Yes
Specific Gravity 0.88200 to 0.89100 @ 25.00 °C.
Pounds per Gallon - (est). 7.339 to 7.414
Refractive Index 1.45950 to 1.46400 @ 20.00 °C.
Melting Point 13.00 to 14.00 °C. @ 760.00 mm Hg
Boiling Point 194.00 to 195.00 °C. @ 1.20 mm Hg
Vapor Pressure 1.000000 mmHg @ 176.00 °C.
Flash Point 235.00 °F. TCC ( 112.78 °C. )
logP (o/w) 7.698 (est)
Soluble in paraffin oil

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesskin conditioning - emollient

Organoleptic Properties

Odor Strength low
Odor Description
at 100.00 %.
at 5.00 %.
Taste Description at 10.00 - 20.00 ppm.

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 25000 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorythickeners, gelling agents, stabalizers and emulsifiers
RIFM Fragrance Material Safety AssessmentSearch
Recommendation for (Z)-oleic acid usage levels up to6.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU)830.00 (μg/capita/day)
baked goods-
beverages(nonalcoholic)0.25000
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
imitation dairy-
instant coffee / tea-
jams / jellies-
meat products-
milk products-
nut products-
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors-
snack foods-
soft candy-
soups-
sugar substitutes-
sweet sauces-

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Potential Uses

FL cheese blue cheese FL cheese cheddar cheese FL cheese swiss cheese emollients emulsifying agents FR orris FL peanut FL peanut butter

Natural Occurrence

almond seed anise seed apple custard apple plant apple fruit apricot fruit apricot seed asparagus shoot avocado fruit baboonwood seed banana fruit banana plant barley leaf barley seed basil seed basswood wood bay laurel fruit bean asparagus bean fruit bean asparagus bean seed bean banner bean seed bean black bean fruit bean black bean seed bean black bean sprout bean butter bean seed bean fava bean seed bean green bean seed bean lima bean seed bean mat bean seed bean mung bean seed bean mung bean sprout bean winged bean leaf bean winged bean seed bean winged bean tuber bean yam bean seed beef cooked beef PMC beet root black gram seed borage seed borage seed oil brazil nut broadbean seed broccoli asparagus broccoli leaf brussel sprout leaf buckthorn sea buckthorn bark buckthorn sea buckthorn fruit buckthorn sea buckthorn seed buckwheat pollen buckwheat seed burdock fruit butternut seed cabbage leaf cacao bean cantaloupe cotyledon cantaloupe seed caper flower caper seed caraway seed cardamom fruit cardamom seed cardamom seed oil carob bean seed carrot root carrot seed cashew nut cassava root cayenne fruit cayenne seed celery plant celery seed celery seed oil chamomile sweet false chamomile plant cheese bleu cheese PMC cheese cheddar cheese PMC cheese swiss cheese PMC cherimoya seed cherry sour cherry fruit cherry sour cherry seed chickpea seed chicory leaf chicory root chicory seed chive leaf cichorium intybus l. root extract @ 0.60% Data cinnamon ceylon cinnamon seed cistus oil @ 1.2% Data coconut seed coffee arabica coffee bean coffee bean coriander fruit coriander seed coriander seed oil corn seed cotton seed cowpea seed cress garden cress leaf cress garden cress seed cucumber cotyledon cucumber fruit cucumber seed cumin seed cumin seed oil currant black currant fruit currant black currant seed oil currant red currant fruit dandelion pollen dandelion root date palm seed dill plant dill seed eggplant fruit elder black elder flower elder black elder leaf endive leaf evening-primrose seed evening-primrose seed oil fennel seed fennel seed oil fenugreek seed fenugreek seed oil fig fruit fig seed flax flower flax seed flax seed oil garlic bulb genet absolute @ 6.00% Data ginger root ginkgo bilob leaf ginkgo bilob seed ginkgo biloba leaf ginkgo biloba seed glycosmis pentaphylla (cor.) bark oil india @ 0.50% Data gooseberry fruit gourd calabash gourd fruit gourd calabash gourd seed gourd wax gourd fruit gourd white gourd fruit grape plant grape seed grape seed oil guava fruit guava seed guava strawberry guava fruit hazelnut nut hazelnut oil ketaki flower oil india @ trace% Data kohlrabi stem lentil seed lentil sprout lettuce leaf lime plant linden little-leaf linden loquat seed lotus indian lotus rhizome lotus indian lotus seed luffa fruit luffa seed lupin white lupin seed lupine white lupine seed macadamia nut mallow jew's mallow leaf mallow jew's mallow seed mandarin fruit mandarin seed oil mango fruit marango seed marjoram seed melon bitter melon cotyledon melon bitter melon fruit melon bitter melon seed moringa seed mushroom shiitake mushroom fruit PMC mustard white mustard mustard white mustard seed nutmeg seed nutmeg seed oil okra seed olive fruit onion bulb onion seed onion seed oil orange fruit oregano plant orris root PMC papaya flower papaya fruit papaya leaf papaya seed papaya seed oil parsley fruit parsley seed parsnip seed passion fruit seed passion seed pea black-eyed pea seed pea black-eyed pea shoot pea fruit pea pigeon pea seed pea seed peach fruit peach seed peanut roasted peanut peanut seed pear fruit pepper bell pepper fruit pepper bell pepper seed pepper black pepper fruit pepper black pepper seed peppermint leaf pine pinyon pine seed pineapple fruit pistachio nut plum fruit plum seed pomegranate seed poppy opium poppy latex poppy opium poppy seed poppy opium poppy seed oil potato sweet potato root potato tuber pumpkin seed purslane herb purslane seed quince seed radish root raspberry red raspberry fruit rice seed roselle seed rosemary leaf rue seed oil rugula seed rye seed safflower seed saffron saffron stigma saffron stigma sage fruit oil sage seed salvia lavandulifolia vahl. leaf oil @ 0.10% Data savory summer savory seed sesame seed sesame seed oil shea tree seed shea tree seed oil sorrel west african sorrel leaf sorrel west african sorrel seed soybean plant soybean seed soybean sprout soybean tissue culture spearmint leaf spinach leaf spinach plant spinach sea spinach leaf squash summer squash fruit star fruit oil cuba @ trace% Data strawberry guava fruit sunflower seed tamarind fruit tamarind seed tamarind seed oil taro leaf taro root tarragon plant tea leaf tea seed oil thyme plant thyme seed tomato fruit walnut black walnut nut walnut english walnut nut watermelon cotyledon watermelon seed wheat plant yam mountain yam root

Synonyms

distoline edenor ATiO5 edenor FTiO5 (Z)- elaidic acid cis- elaidic acid emersol 205 emersol 210 emersol 211 emersol 213 emersol 214NF emersol 233 emersol 6313NF emersol 6321 emersol 6333 NF emersol 7021 extraolein 90 glycon RO glycon WO groco 2 groco 4 groco 5L groco 6 hy-phi 1055 hy-phi 1088 hy-phi 2066 hy-phi 2088 hy-phi 2102 industrene 104 industrene 105 industrene 205 industrene 206 lunac O-CA lunac O-LL lunac OA metaupon neo-fat 90-04 neo-fat 92-04 (9Z)- octadec-9-enoic acid (Z)- octadec-9-enoic acid cis- octadec-9-enoic acid (Z)- octadeca-9-enoic acid (Z)-9- octadecanoic acid cis-9- octadecanoic acid (9Z)- octadecenoic acid (9Z)-9- octadecenoic acid (Z)-9- octadecenoic acid 9-(Z)- octadecenoic acid 9-cis- octadecenoic acid cis-9- octadecenoic acid 9- octadecenoic acid (9Z)- 9- octadecenoic acid (Z)- 9- octadecenoic acid, (9Z)- 9- octadecenoic acid, (Z)- 9- octadecenoic acid, cis- oelsaeure oelsauere oleic acid cis- oleic acid delta9-cis- oleic acid oleic acid 65%--no BHA/BHT added oleic acid N.F. oleic acid natural oleic acid, natural & kosher oleine 7503 oleinic acid pamolyn pamolyn 100 pamolyn 100 FGK kosher oleic acid pamolyn 125 priolene 6900 priolene 6906 priolene 6907 priolene 6928 priolene 6930 priolene 6933 priolene 6936 tego-oleic 130 vopcolene 27 wecoline OO wochem no. 320 PubMed: Perturbation of copper homeostasis is instrumental in early developmental arrest of intraerythrocytic Plasmodium falciparum. PubMed: Oxygenated fatty acids isolated from wheat bran slurries. PubMed: Δ12-Fatty acid desaturase from Candida parapsilosis is a multifunctional desaturase producing a range of polyunsaturated and hydroxylated fatty acids. PubMed: Acinetobacter harbinensis sp. nov., isolated from river water. PubMed: Optimization of lipid enriched biomass production from oleaginous fungus using response surface methodology. PubMed: Baseline resolution of isomers by traveling wave ion mobility mass spectrometry: investigating the effects of polarizable drift gases and ionic charge distribution. PubMed: Cis-9-octadecenoic acid from the rhizospheric bacterium Stenotrophomonas maltophilia BJ01 shows quorum quenching and anti-biofilm activities. PubMed: Inhibition of Mycobacterium tuberculosis PknG by non-catalytic rubredoxin domain specific modification: reaction of an electrophilic nitro-fatty acid with the Fe-S center. PubMed: Liquid chromatography-mass spectrometry-based chemotaxonomic classification of Aspergillus spp. and evaluation of the biological activity of its unique metabolite, neosartorin. PubMed: The rhizobacterium Arthrobacter agilis produces dimethylhexadecylamine, a compound that inhibits growth of phytopathogenic fungi in vitro. PubMed: Characterization and chemical composition of fatty acids content of watermelon and muskmelon cultivars in Saudi Arabia using gas chromatography/mass spectroscopy. PubMed: Triterpene esters and biological activities from edible fruits of Manilkara subsericea (Mart.) Dubard, Sapotaceae. PubMed: Acinetobacter puyangensis sp. nov., isolated from the healthy and diseased part of Populus xeuramericana canker bark. PubMed: Antifungal hydroxy fatty acids produced during sourdough fermentation: microbial and enzymatic pathways, and antifungal activity in bread. PubMed: Hydroxyl octadecenoic acids biosynthesized by crown galls of Panax quinquefolium induced by artermisinic acid. PubMed: Assessment and profiling of the fatty acids in two ackee fruit (Blighia sapida Köenig) varieties during different ripening stages. PubMed: In Silico Studies on Fungal Metabolite against Skin Cancer Protein (4,5-Diarylisoxazole HSP90 Chaperone). PubMed: A study on fatty acids in seeds of Euterpe oleracea Mart seeds. PubMed: Chemical composition and biological activity of Salvia verbenaca essential oil. PubMed: Composition of fatty oils from semen ziziphi spinosae and its cardiotonic effect on isolated toad hearts. PubMed: Fast ultrasound-assisted extraction of polar (phenols) and nonpolar (lipids) fractions in Heterotheca inuloides Cass. PubMed: [Comparison of organic component and di-n-butyl phthalate between human milk and cow milk products]. PubMed: Three new fatty acids from the roots of Boehmeria nivea (L.) Gaudich and their antifungal activities. PubMed: Identification of urinary sex pheromones in female buffaloes and their influence on bull reproductive behaviour. PubMed: Chemical composition and bioactivities of the marine alga Isochrysis galbana from Taiwan. PubMed: [Preparation of Ganoderma lucidum polysaccharides and triterpenes microemulsion and its anticancer effect in mice with transplant Heps tumors]. PubMed: Identification of three genes encoding microsomal oleate desaturases (FAD2) from the oilseed crop Camelina sativa. PubMed: Genetic variants in the FADS gene cluster are associated with arachidonic acid concentrations of human breast milk at 1.5 and 6 mo postpartum and influence the course of milk dodecanoic, tetracosenoic, and trans-9-octadecenoic acid concentrations over the duration of lactation. PubMed: Plasmodium falciparum: differing effects of non-esterified fatty acids and phospholipids on intraerythrocytic growth in serum-free medium. PubMed: Paleic acid, a fatty acid from Paenibacillus sp.: taxonomy, fermentation, isolation, structure determination, and anti-Mannheimia and -Pasteurella activity. PubMed: Variation in amino acid and lipid composition of latent fingerprints. PubMed: Effects of oil source and fish oil addition on ruminal biohydrogenation of fatty acids and conjugated linoleic acid formation in beef steers fed finishing diets. PubMed: Polyunsaturated docosahexaenoic acid suppresses oxidative stress induced endothelial cell calcium influx by altering lipid composition in membrane caveolar rafts. PubMed: Chemical composition and in vitro antimicrobial activity of the volatile oils from Gliomastix murorum and Pichia guilliermondii, two endophytic fungi in Paris polyphylla var. yunnanensis. PubMed: Oxidation of oleic acid at the air-water interface and its potential effects on cloud critical supersaturations. PubMed: An ab initio and DFT study of structure and vibrational spectra of gamma form of oleic acid: comparison to experimental data. PubMed: Two new compounds from transgenic Panax quinquefolium. PubMed: [GC-MS analysis on the chemical constituents of essential oil from bark of Horsfieldia hainanensis]. PubMed: Fabrication of superparamagnetic magnetite/poly(styrene-co-12-acryloxy-9-octadecenoic acid) nanocomposite microspheres with controllable structure. PubMed: [Identification and antibacterial activity of secondary metabolites from Taxus endophytic fungus]. PubMed: Characterization of probiotic carnobacteria isolated from rainbow trout (Oncorhynchus mykiss) intestine. PubMed: Thermodynamics of the clusterization process of cis isomers of unsaturated fatty acids at the air/water interface. PubMed: Infrared spectroscopic study of the effect of oleic acid on the deliquescence behaviour of ammonium sulfate aerosol particles. PubMed: GC-MS analysis of liposoluble constituents from the stems of Cynomorium songaricum. PubMed: Metabolic profiling of transgenic rice with cryIAc and sck genes: an evaluation of unintended effects at metabolic level by using GC-FID and GC-MS. PubMed: Studies on chemical constituents of Gracilaria verrucosa. PubMed: Identification of acylglycerols containing dihydroxy fatty acids in castor oil by mass spectrometry. PubMed: Antioxidant, alpha-amylase inhibitory and brine-shrimp toxicity studies on Centaurea centaurium L. methanolic root extract. PubMed: Two new fatty esters from Rhazya stricta roots (Apocynanaceae). PubMed: Liposomal formulations from phospholipids of Greek almond oil. Properties and biological activity. PubMed: Plasmodium falciparum: Chemically defined medium for continuous intraerythrocytic growth using lipids and recombinant albumin. PubMed: Possible involvement of long chain fatty acids in the spores of Ganoderma lucidum (Reishi Houshi) to its anti-tumor activity. PubMed: [Analysis of the volatile oils chemical constituents of roots of Actinidia deliciosa]. PubMed: A novel preparation of surface-modified paramagnetic magnetite/polystyrene nanocomposite microspheres by radiation-induced miniemulsion polymerization. PubMed: Acinetobacter soli sp. nov., isolated from forest soil. PubMed: Impact of oleic acid (cis-9-octadecenoic acid) on bacterial viability and biofilm production in Staphylococcus aureus. PubMed: [Dynamic changes of cold-resistant substances of overwintering Chilo suppressalis (Walker) larvae]. PubMed: New bioactive fatty acids. PubMed: Ricinoleic acid in common vegetable oils and oil seeds. PubMed: Tetrasphaera remsis sp. nov., isolated from the Regenerative Enclosed Life Support Module Simulator (REMS) air system. PubMed: Second-order standard addition for deconvolution and quantification of fatty acids of fish oil using GC-MS. PubMed: Tetrahydrofurandiols (THF-diols), leukotoxindiols (LTX-diols), and endocrine disruption in rats. PubMed: Isolation of fatty acids with anticancer activity from Protaetia brevitarsis larva. PubMed: Aeromicrobium tamlense sp. nov., isolated from dried seaweed. PubMed: Structural analysis of oligomeric molecules formed from the reaction products of oleic acid ozonolysis. PubMed: Vesicles from docosahexaenoic acid. PubMed: Lipid microencapsulation in starch. PubMed: Kinetic studies of the interaction of fatty acids with phosphatidylcholine vesicles (liposomes). PubMed: Leukotoxin diols from ground corncob bedding disrupt estrous cyclicity in rats and stimulate MCF-7 breast cancer cell proliferation. PubMed: Production of conjugated fatty acids by lactic acid bacteria. PubMed: Polyamines are essential for the synthesis of 2-ricinoleoyl phosphatidic acid in developing seeds of castor. PubMed: [Analysis of ant oil extracted with supercritical CO2 fluid from Polyrhachis vicina by GC-MS]. PubMed: Long-chain fatty acids increase cellular dopamine in an immortalized cell line (MN9D) derived from mouse mesencephalon. PubMed: The novel pathway for ketodiene oxylipin biosynthesis in Jerusalem artichoke (Helianthus tuberosus) tubers. PubMed: Chemical composition of the essential oils of two Alpinia species from Hainan Island, China. PubMed: Gas chromatography-mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA). II. Quantitative determination of cis-EODA in human plasma. PubMed: Ethanol-mediated variations in cellular fatty acid composition and protein profiles of two genotypically different strains of Escherichia coli O157:H7. PubMed: Two distinct pathways for the formation of hydroxy FA from linoleic acid by lactic acid bacteria. PubMed: Linoleic acid epoxide promotes the maintenance of mitochondrial function and active Na+ transport following hypoxia. PubMed: Solid-liquid phase behavior of binary fatty acid mixtures. 2. Mixtures of oleic acid with lauric acid, myristic acid, and palmitic acid. PubMed: Band analysis of temperature-dependent near-infrared spectra of oleic acid in the pure liquid state by the analytic geometric approach. PubMed: Characterisation of castor oil by on-line and off-line non-aqueous reverse-phase high-performance liquid chromatography-mass spectrometry (APCI and UV/MALDI). PubMed: Acute toxicity of fatty acids to the freshwater green alga Selenastrum capricornutum. PubMed: Fatty acid composition of seeds of Satureja thymbra and S. cuneifolia. PubMed: An investigation into the role of calcium in the modulation of rat synaptosomal D-[3H]aspartate transport by docosahexaenoic acid. PubMed: NTP Toxicology and Carcinogenesis Studies of Oleic Acid Diethanolamine Condensate (CAS No. 93-83-4) in F344/N Rats and B6C3F1 Mice (Dermal Studies). PubMed: Gas chromatography-mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA). I. Direct evidence for cis-EODA formation from oleic acid oxidation by liver microsomes and isolated hepatocytes. PubMed: Repellent activity of constituents identified in Foeniculum vulgare fruit against Aedes aegypti (Diptera: Culicidae). PubMed: Lipid content and fatty acid composition in lemon wax. PubMed: Attractant volatiles released by female and male Triatoma infestans (Hemiptera: Reduviidae), a vector of chagas disease: chemical analysis and behavioral bioassay. PubMed: Identification and total synthesis of novel fatty acids from the Siphonarid limpet Siphonaria denticulata. PubMed: The cytotoxicity and chemical constituents of the hexane fraction of Typhonium flagelliforme (Araceace). PubMed: Natural oviposition-deterring chemicals in female cotton bollworm, Helicoverpa armigera (Hubner). PubMed: [Branched alkanes and other apolar compounds produced by the cyanobacterium Microcoleus vaginatus from the Negev desert]. PubMed: Transgenic expression of a delta 12-epoxygenase gene in Arabidopsis seeds inhibits accumulation of linoleic acid. PubMed: In vitro test for the effectiveness of antioxidants as inhibitors of thiyl radical-induced reactions with unsaturated fatty acids. PubMed: Defining mechanisms of toxicity for linoleic acid monoepoxides and diols in Sf-21 cells. PubMed: Analysis of the toxic effects of linoleic acid, 12,13-cis-epoxyoctadecenoic acid, and 12,13-dihydroxyoctadecenoic acid in rabbit renal cortical mitochondria. PubMed: Transformations of 12,13-epoxy-11-hydroxy-9-octadecenoic acid and 4,5-epoxy-N-acetylsphingosine by incubation with liver homogenate and liver microsomes. PubMed: Inhibition of polyunsaturated fatty acid accumulation in plants expressing a fatty acid epoxygenase. PubMed: Monohydroxylation and esterification as determinants of the effects of cis- and trans-9-octadecenoic acids on the permeation of hydrocortisone and 5-fluorouracil across hairless mouse skin in vitro. PubMed: Behenic acid is a cholesterol-raising saturated fatty acid in humans. PubMed: Biotransformation of linoleic acid by Clavibacter sp. ALA2: heterocyclic and heterobicyclic fatty acids. PubMed: Antinociceptive activity of ricinoleic acid, a capsaicin-like compound devoid of pungent properties. PubMed: Dietary stearic acid reduces cholesterol absorption and increases endogenous cholesterol excretion in hamsters fed cereal-based diets. PubMed: The action of soybean lipoxygenase-1 on 12-iodo-cis-9-octadecenoic acid: the importance of C11-H bond breaking. PubMed: Quality characteristics of Canarium schweinfurthii Engl. oil. PubMed: Involvement of the cis/trans isomerase Cti in solvent resistance of Pseudomonas putida DOT-T1E. PubMed: Substrate selectivity of various lipases in the esterification of cis- and trans-9-octadecenoic acid. PubMed: Conversion of unsaturated fatty acids by bacteria isolated from compost. PubMed: Influence of oleic acid on the expression, activation and activity of gelatinase A produced by oncogene-transformed human bronchial epithelial cells. PubMed: In vivo studies of the biosynthesis of vernolic acid in the seed of Vernonia galamensis. PubMed: Codiffusion of propylene glycol and dimethyl isosorbide in hairless mouse skin. PubMed: Hydration of linoleic acid by bacteria isolated from ruminants. PubMed: Long-chain alkenes of the haptophytes Isochrysis galbana and Emiliania huxleyi. PubMed: Strong dependence of the lipid peroxidation product spectrum whether Fe2+/O2 or Fe3+/O2 is used as oxidant. PubMed: Skin penetration enhancing action of cis-unsaturated fatty acids with omega-9, and omega-12-chain lengths. PubMed: Identification of non-heme diiron proteins that catalyze triple bond and epoxy group formation. PubMed: Lipoproteins of Treponema denticola: their effect on human polymorphonuclear neutrophils. PubMed: Intestinal absorption of Mn-mesoporphyrin in a small bowel sac system: effect of oleic acid. PubMed: Mechanism of linoleic acid hydroperoxide reaction with alkali. PubMed: Production of hydroxy fatty acid (10-hydroxy-12(Z)-octadecenoic acid) by Lactobacillus plantarum from linoleic acid and its cardiac effects to guinea pig papillary muscles. PubMed: Fat infiltration in liver of rats induced by different dietary plant oils: high oleic-, medium oleic- and high petroselinic acid-oils. PubMed: Lipid oxidation products in ischemic porcine heart tissue. PubMed: Glucuronic acid-conjugated dihydroxy fatty acids in the urine of patients with generalized peroxisomal disorders. PubMed: Analysis by fast-atom bombardment tandem mass spectrometry of phosphatidylcholine isolated from heart mitochondrial fractions: Evidence of incorporation of monohydroxylated fatty acyl moieties. PubMed: Pre-incubation of synaptosomes with arachidonic acid potentiates inhibition of [3H]D-aspartate transport. PubMed: Fatty acid selectivity of a lipase purified from Vernonia galamensis seed. PubMed: Interaction of manganese-mesoporphyrin with oleic acid vesicles. PubMed: Action of soybean lipoxygenase 1 on 12-iodo-cis-9-octadecenoic acid and 12-bromo-cis-9-octadecenoic acid. PubMed: Trans-9-octadecenoic acid is biologically neutral and does not regulate the low density lipoprotein receptor as the cis isomer does in the hamster. PubMed: Nitric oxide reductase from Pseudomonas stutzeri, a novel cytochrome bc complex. Phospholipid requirement, electron paramagnetic resonance and redox properties. PubMed: Heating unsaturated fatty acids in air produces hemagglutinins. PubMed: Cellular fatty acid composition of Erysipelothrix rhusiopathiae and Erysipelothrix tonsillarum. PubMed: Plasma cholesteryl ester transfer protein activity is increased when trans-elaidic acid is substituted for cis-oleic acid in the diet. PubMed: Solvent effects on lipase-catalyzed esterification of glycerol and fatty acids. PubMed: Validation of reflectance infrared spectroscopy as a quantitative method to measure percutaneous absorption in vivo. PubMed: Fatty acids regulate hepatic low density lipoprotein receptor activity through redistribution of intracellular cholesterol pools. PubMed: Differential effects of cis and trans fatty acid isomers, oleic and elaidic acids, on the cholesteryl ester transfer protein activity. 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