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E4504

Sigma-Aldrich

cis-8,11,14-Eicosatrienoic acid

≥99%

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Synonym(s):
bis-Homo-γ-linolenic acid, Homo-γ-linolenic acid
Linear Formula:
CH3(CH2)3(CH2CH=CH)3(CH2)6CO2H
CAS Number:
Molecular Weight:
306.48
Beilstein/REAXYS Number:
1796533
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

plant oil (Borage)

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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1 of 4

This Item
L1376L1751L2626
vibrant-m

E4504

cis-8,11,14-Eicosatrienoic acid

vibrant-m

L1376

Linoleic acid

vibrant-m

L1751

Ethyl linoleate

vibrant-m

L2626

Methyl linolenate

biological source

plant oil (Borage)

biological source

plant oil (safflower)

biological source

plant oil (safflower)

biological source

plant

functional group

carboxylic acid

functional group

carboxylic acid

functional group

ester

functional group

ester

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

refractive index

n20/D 1.478 (lit.)

refractive index

n20/D 1.466 (lit.)

refractive index

n20/D 1.455 (lit.)

refractive index

n20/D 1.470 (lit.)

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

ambient

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

143.6 °F - closed cup

flash_point_c

62 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


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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
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 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
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-
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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