EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

gamolenic acid
g-linolenic acid

Supplier Sponsors

CAS Number: 506-26-3Picture of molecule3D/inchi
FDA UNII: 78YC2MAX4O
Nikkaji Web:J12.229G
Beilstein Number:1712253
MDL:MFCD00065718
XlogP3-AA:5.90 (est)
Molecular Weight:278.43550000
Formula:C18 H30 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 FDA/DG SANTE Petitions, Reviews, Notices:
GRN 652 Gamma linolenic acid safflower oil View - notice PDF
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 379.50 °C. @ 760.00 mm Hg (est)
Flash Point: 530.00 °F. TCC ( 276.40 °C. ) (est)
logP (o/w): 6.570 (est)
Soluble in:
 water, 0.02371 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
cis,cis,cis-6,9,12-Octadecatrienoic Acid 95%
Sigma-Aldrich
For experimental / research use only.
gamma-Linolenic acid
analytical standard
TCI AMERICA
For experimental / research use only.
gamma-Linolenic Acid >98.0%(GC)(T)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for gamolenic acid usage levels up to:
 not for fragrance use.
 
Recommendation for gamolenic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5280933
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Chemidplus:0000506263
 
References:
 (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5280933
Pubchem (sid):134976478
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C06426
HMDB (The Human Metabolome Database):HMDB03073
FooDB:FDB002943
Export Tariff Code:2916.15.1000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 borage fruit oil
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 borage leaf
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 borage seed
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 borage seed oil
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 carrot seed
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 currant black currant seed
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 currant black currant seed oil
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 evening-primrose seed
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 evening-primrose seed oil
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 flax seed
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 gooseberry seed
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Synonyms:
 gamoleic acid
g-linolenic acid
gamma-linolenic acid
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
(6Z,9Z,12Z)-octadecatrienoic acid
(Z,Z,Z)-6,9,12-octadecatrienoic acid
6-cis,9-cis,12-cis-octadecatrienoic acid
6,9,12-all-cis-octadecatrienoic acid
6(Z),9(Z),12(Z)-octadecatrienoic acid
6Z,9Z,12Z-octadecatrienoic acid
cis-6,cis-9,cis-12-octadecatrienoic acid
cis,cis,cis-6,9,12-octadecatrienoic acid
6,9,12-octadecatrienoic acid, (6Z,9Z,12Z)-
6,9,12-octadecatrienoic acid, (Z,Z,Z)-
 

Articles:

PubMed:Needle core biopsy for the assessment of unilateral breast masses in men.
PubMed:A randomized multicenter study of gamolenic acid (Efamast) with and without antioxidant vitamins and minerals in the management of mastalgia.
PubMed:Nonprescription medicine use in a multiple sclerosis clinic population.
PubMed:Management of cyclical mastalgia in oriental women: pioneer experience of using gamolenic acid (Efamast) in Asia.
PubMed:Drug therapy of mastalgia. What are the options?
PubMed:Effect of oral gamolenic acid from evening primrose oil on menopausal flushing.
PubMed:The use of gamma-linolenic acid in diabetic neuropathy.
PubMed:Gamolenic acid in atopic eczema: Epogam.
 
Notes:
an omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. it is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as pge1. (from merck index, 11th ed) A minor component of many animal lipids Although GLA is an n?6 fatty acid, a type of acid which is generally pro-inflammatory, it has anti-inflammatory properties. (See discussion at Essential fatty acid interactions: The paradox of dietary GLA.); An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed) -- Pubchem; From GLA, the body forms dihomo-?-linolenic acid (DGLA). This is one of the body's three sources of eicosanoids (along with AA and EPA.) DGLA is the precursor of the prostaglandin PGH1, which in turn forms PGE1 and the thromboxane TXA1. PGE1 has a role in regulation of immune system function and is used as the medicine alprostadil. TXA1 modulates the pro-inflammatory properties of the thromboxane TXA2.; GLA is categorized as an n?6 (also called ??6 or omega-6) fatty acid, meaning that the first double bond on the methyl end (designated with n or ?) is the sixth bond. In physiological literature, GLA is designated as 18:3 (n?6). Chemically, GLA is a carboxylic acid with an 18-carbon chain and three cis double bonds. It is an isomer of ?-linolenic acid, which is the n?3 fatty acid found in flax seed.; The human body produces GLA from linoleic acid (LA). This reaction is catalyzed by ?6-desaturase (D6D), an enzyme which allows the creation of a double bond on the sixth carbon counting from the carboxyl terminus. LA is consumed sufficiently in most diets, from such abundant sources as cooking oils and meats. However, a lack of GLA can occur when there is a reduction of the efficiency of the D6D conversion (for instance, as people grow older or when there are specific dietary deficiencies) or in disease states where there is excessive consumption of GLA metabolites.; ?-Linolenic acid (gamma-linolenic acid or GLA, sometimes called gamoleic acid) is a fatty acid found primarily in vegetable oils. It is sold as a dietary supplement for treating problems with inflammation and auto-immune diseases. The efficacy of such use is disputed.
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