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1783-84-2 molecular structure
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(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid

ChemBase ID: 40
Molecular Formular: C20H34O2
Molecular Mass: 306.48276
Monoisotopic Mass: 306.25588033
SMILES and InChIs

SMILES:
OC(=O)CCCCCC/C=C\C/C=C\C/C=C\CCCCC
Canonical 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

Cite this record

CBID:40 http://www.chembase.cn/molecule-40.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
IUPAC Traditional name
dihomo-gamma-linolenic acid
gamma-homolinolenic acid
Brand Name
Tona-lean 1000 CLA (Action Labs)
Star GLA (GNC)
Synonyms
(8E,11E,14E)-8,11,14-Icosatrienoic acid
8,11,14-Eicosatrienoic Acid
(Z,Z,Z)-8,11,14-Eicosatrienoic acid
cis-8,11,14-Eicosatrienoic acid
DGLA
Dihomo-gamma-linolenic acid
Homo-gamma-linolenic acid
gamma-Homolinolenic acid
cis-8,11,14-Eicosatrienoic acid
(8Z,11Z,14Z)-8,11,14-Eicosatrienoic Acid
8,11,14-all-cis-Eicosatrienoic acid
Bishomo-γ-linolenic Acid
Dihomo-γ-linolenic Acid
Ro 12-1989
all-cis-8,11,14-Eicosatrienoic Acid
cis-8,cis-11,cis-14-Eicosatrienoic Acid
γ-Homolinolenic Acid
cis-8,11,14-Eicosatrienoic Acid
Homo-γ-linolenic acid
顺式-8,11,14-二十烷三烯酸甲酯
顺式-8,11,14-二十碳三烯酸
CAS Number
1783-84-2
EC Number
217-233-0
MDL Number
MFCD00065721
Beilstein Number
1796533
PubChem SID
160963503
46508866
24894557
PubChem CID
5280581

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.8858237  H Acceptors
H Donor LogD (pH = 5.5) 6.24093 
LogD (pH = 7.4) 4.4736137  Log P 6.9490924 
Molar Refractivity 98.8374 cm3 Polarizability 37.38399 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds 15 
Lipinski's Rule of Five false 
Log P 7.24  LOG S -6.6 
Solubility (Water) 7.71e-05 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
chloroform: soluble50 mg/mL, clear, colorless expand Show data source
Flash Point
143.6 °F expand Show data source
62 °C expand Show data source
Refractive Index
n20/D 1.478(lit.) expand Show data source
Hydrophobicity(logP)
6.8 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US) expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥99% expand Show data source
≥99.0% (GC) expand Show data source
99% expand Show data source
Certificate of Analysis
Download expand Show data source
Linear Formula
CH3(CH2)3(CH2CH=CH)3(CH2)6CO2H expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich DrugBank DrugBank TRC TRC
Sigma Aldrich - E4504 external link
包装
100 mg in ampule
Sealed ampule.
DrugBank - DB00154 external link
Item Information
Drug Groups approved; nutraceutical
Description A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5. [PubChem]
Indication For nutritional supplementation, also for treating dietary shortage or imbalance
Pharmacology Dihomo gamma-linolenic acid or DHLA is an n-6 (omega-6) polyunsaturated fatty acid. It is comprised of 20 carbon atoms and three double bonds. DHLA is a byproduct of the 18 carbon gamma-linolenic acid (GLA). DHLA is then converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect.
Affected Organisms
Humans and other mammals
External Links
PDRhealth
Toronto Research Chemicals - E477930 external link
cis-8,11,14-Eicosatrienoic acid is a fatty acid which has selective tumoricidal action.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Das, U., et al.: Cancer Lett., 56, 235 (1991)
  • • Rudra, P., et al.: Anticancer Res., 21, 29 (1991)
  • • Menendez, J., et al.: Breast Cancer Res. Treat., 72, 203 (1991)
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PATENTS

PATENTS

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INTERNET

INTERNET

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