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 |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Elaidic acid is the 9-trans isomer of oleic acid. It is a monounsaturated trans-fatty acid, which can be found in partially hydrogenated cooking oils. It was revealed, that elaidic acid inhibits HHT and HETE formation in human platelets incubated with arachidonic acid. Also was shown, that trans oleic acid increased plasma CETP activity, which increases low-density lipoprotein (LDL) cholesterol and decreases high-density lipoprotein (HDL).
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 |
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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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Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses. | 1980 Dec |
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Effect of sodium nitroprusside on cardiovascular function and pulmonary shunt in canine oleic acid pulmonary edema. | 1981 Nov |
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Gender differences in regional fatty acid metabolism before and after meal ingestion. | 1995 Nov |
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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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Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions. | 2000 Jun 20 |
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Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. | 2000 Mar |
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Transdermal delivery of levosimendan. | 2000 Oct |
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Behenic acid is a cholesterol-raising saturated fatty acid in humans. | 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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Novel approach to improve permeation of ondansetron across shed snake skin as a model membrane. | 2001 Jun |
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Bezafibrate attenuates the overexpression of plasminogen activator inhibitor-1 messenger RNA by a combination of mono-unsaturated fatty acid and insulin in hepG2 cells. | 2001 Mar 9 |
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Enhanced GLUT2 gene expression in an oleic acid-induced in vitro fatty liver model. | 2002 Jun |
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Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability. | 2003 Aug |
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Endogenous phospholipase D2 localizes to the plasma membrane of RBL-2H3 mast cells and can be distinguished from ADP ribosylation factor-stimulated phospholipase D1 activity by its specific sensitivity to oleic acid. | 2003 Jan 15 |
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The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids. | 2003 Mar 28 |
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Characterization of a heart-specific fatty acid transport protein. | 2003 May 2 |
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Decreasing IRS-2 expression in pancreatic beta-cells (INS-1) promotes apoptosis, which can be compensated for by introduction of IRS-4 expression. | 2003 Nov 14 |
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Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids. | 2004 Dec |
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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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Fat mobilization in adipose tissue is promoted by adipose triglyceride lipase. | 2004 Nov 19 |
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Dietary trans fatty acids and composition of human atheromatous plaques. | 2004 Oct |
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PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver. | 2006 May |
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Effect of CCK-1 receptor blockade on ghrelin and PYY secretion in men. | 2007 Apr |
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Glucosamine-induced endoplasmic reticulum stress attenuates apolipoprotein B100 synthesis via PERK signaling. | 2009 Sep |
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Activation of group IVC phospholipase A(2) by polycyclic aromatic hydrocarbons induces apoptosis of human coronary artery endothelial cells. | 2011 Jun |
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New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors. | 2012 Nov |
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Oleic acid decreases BCRP mediated efflux of mitoxantrone in Caco-2 cell monolayers. | 2012 Oct |
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Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells. | 2012 Sep |
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Increased autoimmune responses against auto-epitopes modified by oxidative and nitrosative damage in depression: implications for the pathways to chronic depression and neuroprogression. | 2013 Jul |
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Quercetin ameliorate insulin resistance and up-regulates cellular antioxidants during oleic acid induced hepatic steatosis in HepG2 cells. | 2013 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23376733
Rats were gavaged with oleic acid FFA (500 mg/10 mL/kg)
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24548007
Oleic acid noncompetitively attenuated BACE1 activity with a half-maximal inhibitory concentration (IC₅₀) value of 61.31 uM and Ki value of 34.3 uM.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 15:12:27 GMT 2023
by
admin
on
Fri Dec 15 15:12:27 GMT 2023
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Record UNII |
2UMI9U37CP
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Record Status |
Validated (UNII)
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Record Version |
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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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PRIMARY | |||
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D019301
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PRIMARY | |||
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1240
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PRIMARY | |||
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445639
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PRIMARY | |||
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68
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PRIMARY | |||
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16196
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PRIMARY | |||
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204-007-1
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PRIMARY | |||
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70616
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ALTERNATIVE | |||
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7631
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PRIMARY | |||
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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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ALTERNATIVE | |||
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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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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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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 |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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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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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
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LIPID -> FATTY ACID |
dependent on method of extraction
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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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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
Values are % of total.
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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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LIPID -> FATTY ACID |
Value is % of composition.
Oleic safflower variety UC-1 cited by Knowles, P, Calif. Agr. 19(12),15(1965), produced 77.00% by composition.
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SALT/SOLVATE -> PARENT |
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LIPID -> FATTY ACID |
MAY BE PRESENT
USP
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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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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 |
U.S produced rice oil. Values are % of composition.
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
Values given are in undefined precent.
Average is typical for U.S. Sunflower oil.
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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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LIPID -> FATTY ACID |
Values are % of total.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
Value is % of total fatty acids.
Maiti, S, et al; Handbook of Annual Oilseed Crops, OIBH, New Delhi, India(1988), pp.1987-90
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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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LIPID -> FATTY ACID |
TUNISIAN SOURCE
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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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