ContaminantDB: Alpha-Linolenic Acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (12)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:17:40 UTC

Update Date

2016-10-28 10:02:51 UTC

Accession Number

CHEM003769

Identification

Common Name

Alpha-Linolenic Acid

Class

Small Molecule

Description

Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition.

Contaminant Sources

Cosmetic Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
OECD HPV Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Animal Toxin
Dietary Supplement
Drug
Food Toxin
Household Toxin
Metabolite
Micronutrient
Natural Compound
Nutraceutical
Organic Compound
Supplement

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(9,12,15)-Linolenic acid	ChEBI
(9Z,12Z,15Z)-Octadecatrienoic acid	ChEBI
(Z,Z,Z)-9,12,15-Octadecatrienoic acid	ChEBI
9,12,15-Octadecatrienoic acid	ChEBI
9-cis,12-cis,15-cis-Octadecatrienoic acid	ChEBI
ALA	ChEBI
all-cis-9,12,15-Octadecatrienoic acid	ChEBI
cis,cis,cis-9,12,15-Octadecatrienoic acid	ChEBI
cis-Delta(9,12,15)-Octadecatrienoic acid	ChEBI
Linolenic acid	ChEBI
Linolenate	Kegg
alpha-Linolenate	Kegg
(9,12,15)-Linolenate	Generator
(9Z,12Z,15Z)-Octadecatrienoate	Generator
(Z,Z,Z)-9,12,15-Octadecatrienoate	Generator
9,12,15-Octadecatrienoate	Generator
9-cis,12-cis,15-cis-Octadecatrienoate	Generator
all-cis-9,12,15-Octadecatrienoate	Generator
cis,cis,cis-9,12,15-Octadecatrienoate	Generator
cis-delta(9,12,15)-Octadecatrienoate	Generator
cis-Δ(9,12,15)-octadecatrienoate	Generator
cis-Δ(9,12,15)-octadecatrienoic acid	Generator
a-Linolenate	Generator
a-Linolenic acid	Generator
Α-linolenate	Generator
Α-linolenic acid	Generator
alpha Linolenic acid	MeSH
cis-9,12,15-Octadecatrienoate	HMDB
cis-9,12,15-Octadecatrienoic acid	HMDB
Industrene 120	HMDB
FA(18:3(9Z,12Z,15Z))	HMDB
FA(18:3n3)	HMDB

Chemical Formula

C₁₈H₃₀O₂

Average Molecular Mass

278.430 g/mol

Monoisotopic Mass

278.225 g/mol

CAS Registry Number

463-40-1

IUPAC Name

(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid

Traditional Name

α linolenic acid

SMILES

CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-

InChI Key

DTOSIQBPPRVQHS-PDBXOOCHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

omega-3 fatty acid (CHEBI:27432 )
linolenic acid (CHEBI:27432 )
Unsaturated fatty acids (C06427 )
Polyunsaturated fatty acids (C06427 )
Unsaturated fatty acids (LMFA01030152 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Epidermis
Fibroblasts
Intestine
Muscle
Nervous Tissues
Placenta
Platelet
Prostate

Pathways

Name	SMPDB Link	KEGG Link
Alpha Linolenic Acid and Linoleic Acid Metabolism	SMP00018	map00592

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	-16.5°C
Boiling Point	231°C at 1.70E+01 mm Hg
Solubility	0.000124 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.00027 g/L	ALOGPS
logP	6.62	ALOGPS
logP	6.06	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	34.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-052f-7900000000-8765cf82603feb1b448f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-004i-9300000000-302519a616eaed5fcc59	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-005c-9800000000-2d44b3c70e2992b9a812	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052f-7900000000-8765cf82603feb1b448f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-9300000000-302519a616eaed5fcc59	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-005c-9800000000-2d44b3c70e2992b9a812	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052f-5900000000-28710ea35f196c595e03	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052e-6950000000-27037263e74c8119ead0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ds-6931000000-657fa0cc66a206a36409	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-004i-0190000000-aee97e9ea2c7f0783adf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-05nb-9500000000-fb92aefc701027239359	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0aru-9100000000-a5dddfe6f629d1371fac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090000000-2b7bea03a685454dd135	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0090000000-53ddfaed6ce13c37d957	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0090000000-e5350a66361bc63d1071	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0090000000-5731aa5e301022c06813	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0090000000-a18b573ad888d048efa6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-2b7bea03a685454dd135	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-e5350a66361bc63d1071	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-5731aa5e301022c06813	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-004i-0090000000-1d391027db3704d71cb9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-00lr-9210000000-41acd8a55f52afec6d79	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-014i-9000000000-a976b4a80a07eb2c4641	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-497eddf5d738a45f83fb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-0c00ca98901526cb2e26	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-1090000000-35ffce9343fe0d15ea0d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-0090000000-373584fbab950d6676cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0090000000-ae1f482177d0e208165e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00o0-5690000000-20804c8382f14ff0ccf4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-8930000000-9d5e342b1351adc71c20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-4d3e8d1180800a7b4ed5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1090000000-67ab14c068a142dd3c30	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9230000000-403c610d63380e63109a	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Alpha Linolenic Acid or ALA is considered an essential fatty acid because it is required for human health, but cannot be synthesized by humans. It is in fact a plant-derived fatty acid. Humans can synthesize other omega-3 fatty acids from ALA, including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). EPA is a precursor of the series-3 prostaglandins, the series-5 leukotrienes and the series-3 thromboxanes. These eicosanoids have anti-inflammatory and anti-atherogenic properties. ALA metabolites may also inhibit the production of the pro-inflammatory eicosanoids, prostaglandin E2 (PGE2) and leukotriene B4 (LTB4), as well as the pro-inflammatory cytokines, tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 beta (IL-1 beta). Omega-3 fatty acids like ALA and its byproducts can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. They regulate gene expression through their effects on the activity of transcription factors including NF-kappa B and members of the peroxisome proliferator-activated receptor (PPAR) family. Incorporation of ALA and its metabolites in cell membranes can affect membrane fluidity and may play a role in anti-inflammatory activity, inhibition of platelet aggregation and possibly in anti-proliferative actions of ALA. ALA is first metabolized by delta6 desaturease into steridonic acid.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC.

Uses/Sources

For nutritional supplementation and for treating dietary shortage or imbalance.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00132

HMDB ID

HMDB0001388

FooDB ID

FDB012462

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB01388

References

Synthesis Reference

Jean-Pierre Masse, “Therapeutic composition containing alpha-linolenic acid and a compound capable of promoting the passage of the acid through the cell membrane, plant extract comprising the acid and the compound, and process for the preparation of the extract.” U.S. Patent US5002767, issued February, 1986.

MSDS

Link

General References

1. Li, Guihua; Qian, Xiangming; Jiang, Yanchao; Ma, Shushi. Preparation of a-linolenic acid from linseed oil. Zhengzhou Gongcheng Xueyuan Xuebao (2004), 25(3), 13-15.

2. Richieri GV, Ogata RT, Kleinfeld AM: Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB. J Biol Chem. 1994 Sep 30;269(39):23918-30.

3. Bajaj M, Suraamornkul S, Romanelli A, Cline GW, Mandarino LJ, Shulman GI, DeFronzo RA: Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. Diabetes. 2005 Nov;54(11):3148-53.

4. Christensen JH, Fabrin K, Borup K, Barber N, Poulsen J: Prostate tissue and leukocyte levels of n-3 polyunsaturated fatty acids in men with benign prostate hyperplasia or prostate cancer. BJU Int. 2006 Feb;97(2):270-3.

5. Attar-Bashi NM, Frauman AG, Sinclair AJ: Alpha-linolenic acid and the risk of prostate cancer. What is the evidence? J Urol. 2004 Apr;171(4):1402-7.

6. Rastogi SK, Singh J: Effect of chemical penetration enhancer and iontophoresis on the in vitro percutaneous absorption enhancement of insulin through porcine epidermis. Pharm Dev Technol. 2005;10(1):97-104.

7. Allman MA, Pena MM, Pang D: Supplementation with flaxseed oil versus sunflowerseed oil in healthy young men consuming a low fat diet: effects on platelet composition and function. Eur J Clin Nutr. 1995 Mar;49(3):169-78.

8. Fokkema MR, Brouwer DA, Hasperhoven MB, Martini IA, Muskiet FA: Short-term supplementation of low-dose gamma-linolenic acid (GLA), alpha-linolenic acid (ALA), or GLA plus ALA does not augment LCP omega 3 status of Dutch vegans to an appreciable extent. Prostaglandins Leukot Essent Fatty Acids. 2000 Nov;63(5):287-92.

9. Becker CC, Lund P, Holmer G, Jensen H, Sandstrom B: Effects of butter oil blends with increased concentrations of stearic, oleic and linolenic acid on blood lipids in young adults. Eur J Clin Nutr. 1999 Jul;53(7):535-41.