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Dihomo-γ-linolenic acid

CAT: 0804-HY-A0143Size: 5 mg (326.28 mM x 50 μL in Ethanol)Dry Ice: NoHazardous: No
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CAT#:0804-HY-A0143Size:5 mg (326.28 mM x 50 μL in Ethanol)
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Dihomo-γ-linolenic acid (DGLA) is a 20-carbon ω-6 fatty acid, with anti-inflammatory and anti-proliferative activities. Dihomo-γ-linolenic acid attenuates atherosclerosis in the apolipoprotein E deficient mouse model system[1][2][3].
CAS Number
1783-84-2
Product Name Alternative
DGLA; all-cis-8,11,14-Eicosatrienoic acid
UNSPSC
12352211
Hazard Statement
H227, H302
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Neuroscience-Neuromodulation
Field of Research
Cancer; Inflammation/Immunology; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/_8Z,11Z,14Z_-Icosa-8,11,14-trienoic_acid.html
Concentration
326.28 mM * 50 μL in Ethanol
Purity
99.0
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(O)=O
Molecular Formula
C20H34O2
Molecular Weight
306.48
Precautions
H227, H302
References & Citations
[1]Wang X, et al. Multiple roles of dihomo-γ-linolenic acid against proliferation diseases. Lipids Health Dis. 2012 Feb 14;11:25.|[2]Gallagher H, et al. Dihomo-γ-linolenic acid inhibits several key cellular processes associated with atherosclerosis. Biochim Biophys Acta Mol Basis Dis. 2019 Sep 1;1865 (9) :2538-2550.|[3]Yang X, et al. Dihomo-γ-linolenic acid inhibits growth of xenograft tumors in mice bearing human pancreatic cancer cells (BxPC-3) transfected with delta-5-desaturase shRNA. Redox Biol. 2019 Jan;20:236-246.
Shipping Conditions
Blue Ice
Storage Conditions
Solution, -20°C, 2 years
Scientific Category
Natural Products
Clinical Information
Launched
Isoform
Human Endogenous Metabolite

Chemical Information

Dihomo-Gamma-Linolenic Acid

All-cis-icosa-8,11,14-trienoic acid is an icosatrienoic acid having three cis double bonds at positions 8, 11 and 14. It has a role as a nutraceutical, a fungal metabolite and a human metabolite. It is a long-chain fatty acid and a fatty acid 20:3. It is a conjugate acid of an all-cis-icosa-8,11,14-trienoate.

CAS Number1783-84-2
PubChem CID5280581
IUPAC Name(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
Molecular FormulaC20H34O2
Molecular Weight306.5
XLogP7.2
Topological Polar Surface Area37.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count15
Heavy Atom Count22
Formal Charge0
Complexity327
SMILES
CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
InChI
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-
InChIKey
HOBAELRKJCKHQD-QNEBEIHSSA-N
Chemical Structure
2D Structure
2D structure of Dihomo-Gamma-Linolenic Acid
CAS: 1783-84-2
CID: 5280581
Formula: C20H34O2
MW: 306.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight306.5
XLogP37.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count15
Exact Mass306.255880323
Monoisotopic Mass306.255880323
Topological Polar Surface Area37.3 Ų
Heavy Atom Count22
Formal Charge0
Complexity327
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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sc-205291ADihomo-γ-Linolenic Acid methyl ester
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MBS5785813Dihomo-gamma-Linolenic acid methyl ester
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