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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Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions. | 2000 Jun 20 |
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Fatty acid and triglyceride composition of milk fat from lactating Holstein cows in response to supplemental canola oil. | 2001 Apr |
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Effect of gamma-butyrobetaine on fatty liver in juvenile visceral steatosis mice. | 2001 Apr |
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Effects of authentic and VLDL hydrolysis-derived fatty acids on vascular smooth muscle cell growth. | 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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Structural characterization of lipopeptide agonists for the bradykinin B2 receptor. | 2001 Apr 15 |
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Tolerance induction by acylated peptides: suppression of EAE in the mouse with palmitoylated PLP peptides. | 2001 Apr 2 |
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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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A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males. | 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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Breed effects on growth performance, carcass characteristics, fatty acid composition, and palatability attributes in finishing steers. | 2001 Feb |
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Effect of lipopolysaccharide and cytokines on oxidative metabolism in neonatal rat hepatocytes. | 2001 Feb |
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DAG accumulation from saturated fatty acids desensitizes insulin stimulation of glucose uptake in muscle cells. | 2001 Feb |
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5-Hydroxytryptamine 4(a) receptor expressed in Sf9 cells is palmitoylated in an agonist-dependent manner. | 2001 Feb 1 |
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Visualization of a functional Galpha q-green fluorescent protein fusion in living cells. Association with the plasma membrane is disrupted by mutational activation and by elimination of palmitoylation sites, but not be activation mediated by receptors or AlF4-. | 2001 Feb 9 |
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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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OspA, a lipoprotein antigen of the obligate intracellular bacterial pathogen Piscirickettsia salmonis. | 2001 Jan |
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Effect of long-chain fatty acids in the culture medium on fatty acid composition of WEHI-3 and J774A.1 cells. | 2001 Jan |
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Relationship between the concentrations of plasma phospholipid stearic acid and plasma lipoprotein lipids in healthy men. | 2001 Jan |
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Characterization of a new member of the fatty acid-binding protein family that binds all-trans-retinol. | 2001 Jan 12 |
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Interaction between the unphosphorylated receptor with high affinity for IgE and Lyn kinase. | 2001 Jan 12 |
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Functional analysis of mutant human carnitine acylcarnitine translocases in yeast. | 2001 Jan 26 |
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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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Acylation of lysine 983 is sufficient for toxin activity of Bordetella pertussis adenylate cyclase. Substitutions of alanine 140 modulate acylation site selectivity of the toxin acyltransferase CyaC. | 2001 Jan 5 |
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Insulin inhibits peroxisomal fatty acid oxidation in isolated rat hepatocytes. | 2001 Jun |
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Systemic and regional free fatty acid metabolism in type 2 diabetes. | 2001 Jun |
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Demonstration of direct effects of growth hormone on neonatal cardiomyocytes. | 2001 Jun 22 |
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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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Effects of diets enriched in n-6 or n-3 fatty acids on cholesterol metabolism in older rats chronically fed a cholesterol-enriched diet. | 2001 Mar |
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Brain and hippocampus fatty acid composition in phospholipid classes of aged-relative cognitive deficit rats. | 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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Purification and characterization of the fatty acid synthase from Bugula neritina. | 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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Free fatty acids, but not ketone bodies, protect diabetic rat hearts during low-flow ischemia. | 2001 Mar |
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Increased uncoupling proteins and decreased efficiency in palmitate-perfused hyperthyroid rat heart. | 2001 Mar |
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Flux-balance analysis of mitochondrial energy metabolism: consequences of systemic stoichiometric constraints. | 2001 Mar |
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Glucose metabolism in perfused mouse hearts overexpressing human GLUT-4 glucose transporter. | 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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[Branched alkanes and other apolar compounds produced by the cyanobacterium Microcoleus vaginatus from the Negev desert]. | 2001 Mar-Apr |
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The sites for fatty acylation, phosphorylation and intermolecular disulphide bond formation of influenza C virus CM2 protein. | 2001 May |
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A high-sucrose diet increases gluconeogenic capacity in isolated periportal and perivenous rat hepatocytes. | 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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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
Fri Dec 16 15:55:43 UTC 2022
by
admin
on
Fri Dec 16 15:55:43 UTC 2022
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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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Classification Tree | Code System | Code | ||
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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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LOINC |
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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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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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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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 |
USP
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SALT/SOLVATE -> PARENT |
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LIPID -> FATTY ACID |
VARIES ACCORDING TO METHOD OF EXTRACTION.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT | |||
|
SALT/SOLVATE -> PARENT |
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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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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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LIPID -> FATTY ACID |
U.S produced rice oil. Values are % of composition.
|
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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 |
TURKISH SOURCE
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LIPID -> FATTY ACID |
Values are % of total.
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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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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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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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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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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 |
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 |
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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