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E4504

Sigma-Aldrich

cis-8,11,14-Eicosatrienoic acid

≥99%

Synonym(s):

bis-Homo-γ-linolenic acid, Homo-γ-linolenic acid

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About This Item

Linear Formula:
CH3(CH2)3(CH2CH=CH)3(CH2)6CO2H
CAS Number:
1783-84-2
Molecular Weight:
306.48
Beilstein:
1796533
EC Number:
217-233-0
MDL number:
MFCD00065721
UNSPSC Code:
12352211
PubChem Substance ID:
24894557
NACRES:
NA.25

biological source

plant oil (Borage)

Quality Level

200

Assay

≥99%

form

viscous liquid

refractive index

n20/D 1.478 (lit.)

functional group

carboxylic acid

lipid type

omega FAs

shipped in

ambient

storage temp.

−20°C

SMILES string

CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O

InChI

1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-

InChI key

HOBAELRKJCKHQD-QNEBEIHSSA-N

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Related Categories

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

143.6 °F - closed cup

Flash Point(C)

62 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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C Thijs et al.
European journal of clinical nutrition, 54(3), 234-238 (2000-03-14)
To evaluate whether levels of n-6 long chain polyunsaturated fatty acids (LCPs) in human breast milk are related to the mother's atopic constitution, and whether a decreased level can be restored by gamma-linolenic acid supplementation. Cross-sectional study and dietary supplementation
R M Hamilton et al.
Lipids, 16(5), 374-376 (1981-05-01)
Possible relationships between zinc and essential fatty acid metabolism have been assessed using plasma samples obtained from 39 cystic fibrosis patients. The fatty acid composition of plasma phospholipids was analyzed by capillary gas liquid chromatography and zinc levels were measured
Liping Du et al.
The Journal of pharmacology and experimental therapeutics, 316(1), 371-379 (2005-09-20)
The epidermis expresses cyclooxygenases, lipoxygenases, and cytochromes P450, which utilize arachidonic acid to generate a diverse array of lipid mediators affecting epidermal cellular differentiation and functions. Recent studies show that mouse epidermis expresses CYP2B19, a keratinocyte-specific epoxygenase that generates 11,12-
R D Abraham et al.
Atherosclerosis, 81(3), 199-208 (1990-04-01)
Low levels of essential polyunsaturated fatty acids of the n-6 series are associated with coronary heart disease. Linoleic acid, but not gamma-linolenic acid requires the activity of delta 6-desaturase for its conversion to dihomo-gamma-linolenic and arachidonic acid. Evening primrose oil
B C Melnik et al.
Journal of the American Academy of Dermatology, 21(3 Pt 1), 557-563 (1989-09-01)
Our hypothesis on the origin of atopy links alterations in omega-6-fatty acid metabolism in atopic persons (i.e., reduced formation of delta-6-desaturase products) to deficient T cell differentiation and function. We suggest that a relative deficiency in dihomo-gamma-linolenic acid-derived prostaglandin E1
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