Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H34O2 |
Molecular Weight | 282.4614 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCC\C=C/CCCCCCCC(O)=O
InChI
InChIKey=ZQPPMHVWECSIRJ-KTKRTIGZSA-N
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
Molecular Formula | C18H34O2 |
Molecular Weight | 282.4614 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Oleic acid is an unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Oleic acid occurs naturally in various animal and vegetable fats and oils. It is a component of the normal human diet as a part of animal fats and vegetable oils. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil. Oleic acid has being shown to have a potential anticancer activity.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11478373
Curator's Comment: It was demonstrated that the 18 carbon-monocarboxylic fatty acids, linoleic acid with two cis-double bonds entered brain, whereas oleic acid, with one cis-double bond, did not enter brain. It was concluded the entry of essential fatty acids into brain is accomplished in a highly selective and discrete manner
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL4822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24548007 |
61.31 µM [IC50] | ||
Target ID: CHEMBL3455 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24191036 |
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Target ID: CHEMBL612542 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25430075 |
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Target ID: CHEMBL2083 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17502136 |
185.0 nM [Ki] | ||
Target ID: P11597 Gene ID: 1071.0 Gene Symbol: CETP Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8018112 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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PubMed
Title | Date | PubMed |
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Fatty acids and derivatives as antimicrobial agents. | 1972 Jul |
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Induction of fatty acid binding protein by peroxisome proliferators in primary hepatocyte cultures and its relationship to the induction of peroxisomal beta-oxidation. | 1990 Apr 23 |
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Hypothalamic modulation of growth hormone secretion in the rhesus monkey: evidence from intracerebroventricular infusions of glucose, free fatty acid, and ketone bodies. | 1991 Oct |
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Physiology and pathophysiology of organic acids in cerebrospinal fluid. | 1993 |
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Involvement of endogenous cholecystokinin and somatostatin in gastroprotection induced by intraduodenal fat. | 1998 |
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Effect of fatty acid chain length and saturation on the gastrointestinal handling and metabolic disposal of dietary fatty acids in women. | 1999 Jan |
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Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. | 1999 Jul 14 |
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Fat and mesenteric blood flow. | 1999 Sep |
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Identification of the major intestinal fatty acid transport protein. | 1999 Sep |
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Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in Man. | 2000 |
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Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. | 2000 Mar |
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Long-chain fatty acids regulate liver carnitine palmitoyltransferase I gene (L-CPT I) expression through a peroxisome-proliferator-activated receptor alpha (PPARalpha)-independent pathway. | 2001 Feb 15 |
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The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells. | 2001 Jan |
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Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates. | 2001 Jan 15 |
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Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation. | 2001 Jan-Feb |
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Fatty acids alter monolayer integrity, paracellular transport, and iron uptake and transport in Caco-2 cells. | 2003 Dec |
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A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs. | 2003 Feb 7 |
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What does the measurement of whole-body fatty acid rate of appearance in plasma by using a fatty acid tracer really mean? | 2003 Jul |
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Exchanging carbohydrates for monounsaturated fats in energy-restricted diets: effects on metabolic profile and other cardiovascular risk factors. | 2003 Jun |
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Effects of rosiglitazone and oleic acid on UCP-3 expression in L6 myotubes. | 2003 Mar |
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Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40. | 2003 Mar 13 |
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Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization. | 2003 Oct 15 |
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Stearoyl-CoA desaturase 1 gene expression is necessary for fructose-mediated induction of lipogenic gene expression by sterol regulatory element-binding protein-1c-dependent and -independent mechanisms. | 2004 Jun 11 |
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Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. | 2005 Nov |
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High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids? | 2006 Aug |
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Albumin-bound fatty acids induce mitochondrial oxidant stress and impair antioxidant responses in proximal tubular cells. | 2006 Aug |
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Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. | 2006 Aug |
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Dual inhibition of mycobacterial fatty acid biosynthesis and degradation by 2-alkynoic acids. | 2006 Mar |
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Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element. | 2007 Mar |
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Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids. | 2008 Jul |
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Regulation of fat-stimulated neurotensin secretion in healthy subjects. | 2008 May |
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Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus. | 2008 Sep |
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Role of fat hydrolysis in regulating glucagon-like Peptide-1 secretion. | 2010 Feb |
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PKC activation by resveratrol derivatives with unsaturated aliphatic chain. | 2012 |
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Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line. | 2012 Oct 15 |
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Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells. | 2012 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8018112
diet, containing 15% energy as fat from dairy products, meat, bread and cereals, was supplemented with oleic or elaidic acid
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9920140
It was studied the impact of both cis and trans forms of C 18:1 fatty acids. It was found that cis and trans vaccenic acid (cis and trans C 18:1 delta11), as well as oleic acid (cis C 18:1 delta9) and elaidic acid (trans 18:1 delta9), caused a dose-dependent increase in glucose (16.7 mmol/L)-stimulated insulin secretion during static islet incubations. The maximal stimulatory effect for cis and trans vaccenic acid and for oleic and elaidic acid was observed at concentrations of 2.0 and 3.0 mmol/L, respectively. The trans isomers, trans vaccenic and elaidic acid, elicited a higher maximal insulin output than the respective cis isomers, cis vaccenic and oleic acid. In the presence of another insulin secretagogue, L-leucine, trans vaccenic but not elaidic acid caused a higher response than their cis isomeric fatty acids.
Substance Class |
Chemical
Created
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Record UNII |
2UMI9U37CP
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
31702
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LOINC |
2673-2
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CFR |
21 CFR 172.210
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LOINC |
35166-8
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LOINC |
75102-4
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CFR |
21 CFR 172.862
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CFR |
21 CFR 172.860
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LOINC |
47713-3
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LOINC |
27108-0
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DSLD |
262 (Number of products:639)
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JECFA EVALUATION |
OLEIC ACID
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LOINC |
74620-6
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LOINC |
74621-4
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Code System | Code | Type | Description | ||
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C68405
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2UMI9U37CP
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PRIMARY | |||
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CHEMBL8659
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PRIMARY | |||
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2UMI9U37CP
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PRIMARY | |||
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3400
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D019301
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1240
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445639
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68
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16196
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204-007-1
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70616
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7631
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DTXSID1025809
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112-80-1
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OLEIC ACID
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1478130
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9856
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32559
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DB04224
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100000091945
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SUB12542MIG
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m8191
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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LIPID -> FATTY ACID | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
JB Rossell and co-workers; JAOCS62(2), 221-230(1985).
Range weight is a mean.
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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LIPID -> FATTY ACID | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
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LIPID -> FATTY ACID |
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LIPID -> FATTY ACID |
G Jurriens and ACJ Kroesen, J Am Oil Chem Soc, 42(9)(1965)(average value).
Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
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PARENT -> CONSTITUENT ALWAYS PRESENT |
From Cannabis seed oil.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID | |||
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LIPID -> FATTY ACID |
Values are % of weight of fatty acid composition.
O?Connor, RT, Herb, SF; J Am Oil Chem Soc 47, 186A, 195A, 197A(1970)(range)
Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
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PARENT -> CONSTITUENT ALWAYS PRESENT |
MAJOR
AMOUNT PRESENT
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SALT/SOLVATE -> PARENT |
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LIPID -> FATTY ACID |
MAY BE PRESENT
USP
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LIPID -> FATTY ACID | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT |
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LIPID -> FATTY ACID | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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SALT/SOLVATE -> PARENT |
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LIPID -> FATTY ACID | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Compound measured as 1.60% of the composition of the steam distillate of Elymus repens rhizome as per R Boesel in Planta Medica iss:4 pg:399-400, 1989.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
MAJOR
AMOUNT PRESENT
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LIPID -> FATTY ACID |
Value is fatty acid composition (%) for US corn oil w/std. deviation of 0.90%
LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
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LIPID -> FATTY ACID |
Value is fatty acid composition (%) for international corn oil w/std. deviation of 2.5%
LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
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