Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H32O2 |
Molecular Weight | 256.4241 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCC(O)=O
InChI
InChIKey=IPCSVZSSVZVIGE-UHFFFAOYSA-N
InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)
Molecular Formula | C16H32O2 |
Molecular Weight | 256.4241 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26393565Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12496284 | https://www.ncbi.nlm.nih.gov/pubmed/14717706 | https://www.ncbi.nlm.nih.gov/pubmed/18511927 | https://www.ncbi.nlm.nih.gov/pubmed/23406428
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26393565
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12496284 | https://www.ncbi.nlm.nih.gov/pubmed/14717706 | https://www.ncbi.nlm.nih.gov/pubmed/18511927 | https://www.ncbi.nlm.nih.gov/pubmed/23406428
Palmitic acid is a saturated fatty acid, the principal constituent of refined palm oil, present in the diet and synthesized endogenously. Palmitic acid is able to activate the orphan G protein-coupled receptor GPR40. Palmitic acid was also a weak ligand of peroxisome proliferator-activated receptor gamma. Palmitic acid is a ligand of lipid chaperones - the fatty acid-binding proteins (FABPs). Dietary palm oil and palmitic acid may play a role in the development of obesity, type 2 diabetes mellitus, cardiovascular diseases and cancer.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL4422 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12496284 |
5.3 null [pEC50] | ||
Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14717706 |
156.0 µM [Kd] | ||
Target ID: CHEMBL3344 |
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Target ID: CHEMBL2083 |
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Target ID: CHEMBL3674 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | SURFAXIN Approved UseSURFAXIN is indicated for the prevention of respiratory distress syndrome
(RDS) in premature infants at high risk for RDS. Launch Date1.33090561E12 |
PubMed
Title | Date | PubMed |
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Identification of fatty acid molecules in a Fasciola hepatica immunoprophylactic fatty acid-binding protein. | 2001 Apr |
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Carotenoid esters in vegetables and fruits: a screening with emphasis on beta-cryptoxanthin esters. | 2001 Apr |
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Uncoupling protein 2: a possible link between fatty acid excess and impaired glucose-induced insulin secretion? | 2001 Apr |
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Utility of high performance liquid chromatography/electrospray/mass spectrometry of polar lipids in specifically Per-13C labeled Gram-negative bacteria DA001 as a tracer for acceleration of bioremediation in the subsurface. | 2001 Apr |
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Lysosomal-type PLA2 and turnover of alveolar DPPC. | 2001 Apr |
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Structural characterization of lipopeptide agonists for the bradykinin B2 receptor. | 2001 Apr 15 |
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Kinetics of the lipase-catalyzed synthesis of glucose esters in acetone. | 2001 Apr 20 |
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Induction of apoptosis through B-cell receptor cross-linking occurs via de novo generated C16-ceramide and involves mitochondria. | 2001 Apr 27 |
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Fatty acid-induced apoptosis in neonatal cardiomyocytes: redox signaling. | 2001 Feb |
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Lipotoxicity of the pancreatic beta-cell is associated with glucose-dependent esterification of fatty acids into neutral lipids. | 2001 Feb |
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Myocardial fatty acid oxidation in patients with impaired glucose tolerance. | 2001 Feb |
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Effect of fatty acids on phase behavior of hydrated dipalmitoylphosphatidylcholine bilayer: saturated versus unsaturated fatty acids. | 2001 Feb |
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Breed effects on growth performance, carcass characteristics, fatty acid composition, and palatability attributes in finishing steers. | 2001 Feb |
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The growth inhibitory effect of conjugated linoleic acid on a human hepatoma cell line, HepG2, is induced by a change in fatty acid metabolism, but not the facilitation of lipid peroxidation in the cells. | 2001 Feb 26 |
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L-carnitine reduces malondialdehyde concentrations in isolated rat hearts in dependence on perfusion conditions. | 2001 Jan |
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The composition of saturated fatty acids in plasma phospholipids changes in a way to counteract changes in the mean melting point during pregnancy. | 2001 Jan |
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Alteration of fatty acid profiles in different pulmonary surfactant phospholipids in acute respiratory distress syndrome and severe pneumonia. | 2001 Jan |
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Endogenous surfactant turnover in preterm infants with respiratory distress syndrome studied with stable isotope lipids. | 2001 Jan |
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OspA, a lipoprotein antigen of the obligate intracellular bacterial pathogen Piscirickettsia salmonis. | 2001 Jan |
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Determination of retinoids in galenicals by column liquid chromatography with fluorescence and diode-array detection. | 2001 Jan 5 |
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Insulin inhibits peroxisomal fatty acid oxidation in isolated rat hepatocytes. | 2001 Jun |
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Gbeta gamma isoforms selectively rescue plasma membrane localization and palmitoylation of mutant Galphas and Galphaq. | 2001 Jun 29 |
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Optimization of methods and treatment conditions for studying effects of fatty acids on cell growth. | 2001 Mar |
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Gas chromatographic analysis of total fatty acids in cider. | 2001 Mar |
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Effects of antiinflammatory triterpenes isolated from Leptadenia hastata latex on keratinocyte proliferation. | 2001 Mar |
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Atomic resolution structure analysis of beta' polymorph crystal of a triacylglycerol: 1,2-dipalmitoyl-3-myristoyl-sn-glycerol. | 2001 Mar |
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Cyclooxygenase-2 inhibitory cerebrosides from phytolaccae radix. | 2001 Mar |
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JlpA, a novel surface-exposed lipoprotein specific to Campylobacter jejuni, mediates adherence to host epithelial cells. | 2001 Mar |
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Purification and characterization of the fatty acid synthase from Bugula neritina. | 2001 Mar |
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Development and characterization of an animal model of carnitine deficiency. | 2001 Mar |
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Palmitoylation of the luteinizing hormone/human chorionic gonadotropin receptor regulates receptor interaction with the arrestin-mediated internalization pathway. | 2001 Mar |
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Direct regulatory effect of fatty acids on macrophage lipoprotein lipase: potential role of PPARs. | 2001 Mar |
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Role of fatty acids in the recovery of cardiac function during resuscitation from hemorrhagic shock. | 2001 Mar |
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Macrophages transfer [14C]-labelled fatty acids to pancreatic islets in culture. | 2001 Mar |
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Expression of rat liver long-chain acyl-CoA synthetase and characterization of its role in the metabolism of R-ibuprofen and other fatty acid-like xenobiotics. | 2001 Mar 15 |
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Regulation of G proteins by covalent modification. | 2001 Mar 26 |
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Phospholipids reacylation and palmitoylcoa control tumour necrosis factor-alpha sensitivity. | 2001 Mar 7 |
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Molecular dynamics simulations of stratum corneum lipid models: fatty acids and cholesterol. | 2001 Mar 9 |
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De novo synthesis and recycling pathways of sphingomyelin in rat Sertoli cells. | 2001 Mar 9 |
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[Branched alkanes and other apolar compounds produced by the cyanobacterium Microcoleus vaginatus from the Negev desert]. | 2001 Mar-Apr |
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Thiazolidinediones increase plasma-adipose tissue FFA exchange capacity and enhance insulin-mediated control of systemic FFA availability. | 2001 May |
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Heparin-induced release of protein-bound solutes during hemodialysis is an in vitro artifact. | 2001 May |
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Effects of lung surfactant proteins, SP-B and SP-C, and palmitic acid on monolayer stability. | 2001 May |
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Effects of free fatty acids on beta-cell functions: a possible involvement of peroxisome proliferator-activated receptors alpha or pancreatic/duodenal homeobox. | 2001 May |
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Imaging of monolayers composed of palmitic acid and lung surfactant protein B. | 2001 May |
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n-6 and n-3 polyunsaturated fatty acids differentially modulate oncogenic Ras activation in colonocytes. | 2001 May |
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Palmitoylation of caveolin-1 in endothelial cells is post-translational but irreversible. | 2001 May 11 |
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Differential palmitoylation of two mouse glutamate receptor interacting protein 1 forms with different N-terminal sequences. | 2001 May 18 |
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Biochemical characterization of the reverse activity of rat brain ceramidase. A CoA-independent and fumonisin B1-insensitive ceramide synthase. | 2001 May 18 |
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Physiological levels of mammalian uncoupling protein 2 do not uncouple yeast mitochondria. | 2001 May 25 |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18710535
The conditioned media from palmitic acid (0.2 mM) treated rat cortical astroglia, but not the cerebellar astroglia, significantly elevated levels of phosphorylated tau and BACE1 in cortical neurons as compared to controls
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:33:06 UTC 2023
by
admin
on
Wed Jul 05 22:33:06 UTC 2023
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Record UNII |
2V16EO95H1
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Record Status |
Validated (UNII)
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Record Version |
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LOINC |
47641-6
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NCI_THESAURUS |
C68421
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LOINC |
55873-4
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2719-3
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EU-Orphan Drug |
EU/3/04/217
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LOINC |
74625-5
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DSLD |
1603 (Number of products:186)
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LOINC |
75115-6
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NCI_THESAURUS |
C68388
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LOINC |
35161-9
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JECFA EVALUATION |
PALMITIC ACID
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CFR |
21 CFR 172.860
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CFR |
21 CFR 357.210
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LOINC |
74624-8
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5030
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LL-31
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15756
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1492007
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PALMITIC ACID
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57-10-3
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100000091751
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M8367
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5001
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CHEMBL82293
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C61873
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1426390
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SUB14744MIG
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985
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2V16EO95H1
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200-312-9
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7896
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2V16EO95H1
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DB03796
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1370621
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D019308
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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LIPID -> FATTY ACID |
Value is fatty acid composition (%) for international corn oil w/std. deviation of 1.4%
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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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 |
VARIES ACCORDING TO METHOD OF EXTRACTION.
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SALT/SOLVATE -> PARENT |
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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 4.5% by 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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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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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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PARENT -> CONSTITUENT ALWAYS PRESENT |
Compound measured as 23.50% 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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SALT/SOLVATE -> PARENT | |||
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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 | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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LIPID -> FATTY ACID |
Value is fatty acid composition (%) for US corn oil w/std. deviation of 0.55%
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 |
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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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
U.S produced rice oil. Values are % of composition.
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LIPID -> FATTY ACID |
Values are % of total.
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
TURKISH SOURCE
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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LIPID -> FATTY ACID |
MAY BE PRESENT
USP
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LIPID -> FATTY ACID |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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LIPID -> FATTY ACID |
Values are % of total.
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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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ACTIVE MOIETY |
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