| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:10:27 -0700 |
| HMDB ID |
HMDB01388 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Alpha-Linolenic acid |
| Description |
Alpha-linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. Alpha-linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid (ALA). Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like a-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability and the activity of membrane bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. Alpha linolenic acid and other omega 3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator activated receptors (PPARs) and liver X receptors (LXRs). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- (9,12,15)-linolenate
- (9,12,15)-linolenic acid
- (9Z,12Z,15Z)-Octadecatrienoate
- (9Z,12Z,15Z)-Octadecatrienoic acid
- (Z,Z,Z)-9,12,15-Octadecatrienoate
- (Z,Z,Z)-9,12,15-Octadecatrienoic acid
- 9,12,15-Octadecatrienoate
- 9,12,15-Octadecatrienoic acid
- 9-cis,12-cis,15-cis-Octadecatrienoate
- 9-cis,12-cis,15-cis-Octadecatrienoic acid
- a-Linolenate
- a-Linolenic acid
- All-cis-9,12,15-Octadecatrienoate
- All-cis-9,12,15-Octadecatrienoic acid
- alpha-Linolenate
- alpha-Linolenic acid
- cis,cis,cis-9,12,15-Octadecatrienoate
- cis,cis,cis-9,12,15-Octadecatrienoic acid
- cis-9,12,15-Octadecatrienoate
- cis-9,12,15-Octadecatrienoic acid
- Industrene 120
- Linolenate
- Linolenic acid
|
| Chemical Formula |
C18H30O2 |
| Average Molecular Weight |
278.4296 |
| Monoisotopic Molecular Weight |
278.224580204 |
| IUPAC Name |
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid |
| Traditional IUPAC Name |
α-linolenic acid |
| CAS Registry Number |
463-40-1 |
| 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 |
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Lineolic Acids and Derivatives |
| Sub Class |
N/A |
| Other Descriptors |
- Aliphatic Acyclic Compounds
- Organic Compounds
- Polyunsaturated fatty acids(KEGG)
- Straight Chain Fatty Acids
- Unsaturated Fatty Acids
- Unsaturated fatty acids(KEGG)
- Unsaturated fatty acids(Lipidmaps)
- linolenic acid(ChEBI)
- omega-3 fatty acid(ChEBI)
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| Substituents |
- Acyclic Alkene
- Carboxylic Acid
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| Direct Parent |
Lineolic Acids and Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Essential fatty acid
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
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| Physical Properties |
| State |
Liquid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
-16.5 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
6.46 |
SANGSTER (1993) |
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| Predicted Properties |
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| Spectra |
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| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
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| Biofluid Locations |
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| Tissue Location |
- Muscle
- Fibroblasts
- Intestine
- Placenta
- Epidermis
- Prostate
- Adipose Tissue
- Platelet
- Nervous Tissues
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| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Alpha Linolenic Acid and Linoleic Acid Metabolism |
SMP00018
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map00592
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| Normal Concentrations |
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| Blood |
Detected and Quantified |
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5.11 +/- 3.8 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
17.5 +/- 7.6 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
16.8 +/- 7.3 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
18.5 +/- 7.9 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
1.1 +/- 0.8 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
1.975 +/- 1.223 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.115 +/- 0.004 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.73 +/- 0.54 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Normal |
Not Available |
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| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
21.2 +/- 7.2 uM |
Adult (>18 years old) |
Both |
Hypertension |
Not Available |
| Blood |
Detected and Quantified |
|
20.5 +/- 7.5 uM |
Adult (>18 years old) |
Male |
Essential hypertension |
Not Available |
| Blood |
Detected and Quantified |
|
22.7 +/- 6.2 uM |
Adult (>18 years old) |
Female |
Essential hypertension |
Not Available |
| Urine |
Detected and Quantified |
|
0.49 +/- 0.46 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Cancer |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
| Hypertension |
- Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32.
Pubmed: 18633173
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| Essential hypertension |
- Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32.
Pubmed: 18633173
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| Thyroid cancer |
- Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9.
Pubmed: 14643447
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| Associated OMIM IDs |
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| External Links |
| DrugBank ID |
DB00132  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB012462 |
| KNApSAcK ID |
C00007247  |
| Chemspider ID |
4444437  |
| KEGG Compound ID |
C06427  |
| BioCyc ID |
LINOLENIC_ACID  |
| BiGG ID |
48237  |
| Wikipedia Link |
Linolenic acid  |
| NuGOwiki Link |
HMDB01388  |
| Metagene Link |
HMDB01388  |
| METLIN ID |
6208  |
| PubChem Compound |
5280934  |
| PDB ID |
LNL  |
| ChEBI ID |
27432  |
| References |
| Synthesis Reference |
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. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- 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.
Pubmed: 16430627
- 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.
Pubmed: 15017185
- 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.
Pubmed: 15776817
- 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.
Pubmed: 7774533
- 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.
Pubmed: 11090255
- 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.
Pubmed: 10452408
- Jones DB, Scaretto L, Carter R, Mann JI: Glucose, insulin and platelet fatty acids following myocardial infarction: an association with infarct size. Diabete Metab. 1987 Jul-Aug;13(4):463-6.
Pubmed: 3315767
- Crastes de Paulet A, Babin F, Billeaud C, Bougle D, Sarda P, Mendy F: [Biological effects on premature neonates of a milk formula enriched with alpha-linolenic acid: a multicenter study] Bull Acad Natl Med. 1994 Feb;178(2):267-73; discussion 273-8.
Pubmed: 7913655
- 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.
Pubmed: 7929039
- Li D, Sinclair A, Wilson A, Nakkote S, Kelly F, Abedin L, Mann N, Turner A: Effect of dietary alpha-linolenic acid on thrombotic risk factors in vegetarian men. Am J Clin Nutr. 1999 May;69(5):872-82.
Pubmed: 10232625
- Bhatia KS, Singh J: Effect of linolenic acid/ethanol or limonene/ethanol and iontophoresis on the in vitro percutaneous absorption of LHRH and ultrastructure of human epidermis. Int J Pharm. 1999 Apr 15;180(2):235-50.
Pubmed: 10370194
- Baylin A, Kabagambe EK, Ascherio A, Spiegelman D, Campos H: Adipose tissue alpha-linolenic acid and nonfatal acute myocardial infarction in Costa Rica. Circulation. 2003 Apr 1;107(12):1586-91. Epub 2003 Mar 10.
Pubmed: 12668490
- Williard DE, Nwankwo JO, Kaduce TL, Harmon SD, Irons M, Moser HW, Raymond GV, Spector AA: Identification of a fatty acid delta6-desaturase deficiency in human skin fibroblasts. J Lipid Res. 2001 Apr;42(4):501-8.
Pubmed: 11290821
- Campbell FM, Gordon MJ, Dutta-Roy AK: Preferential uptake of long chain polyunsaturated fatty acids by isolated human placental membranes. Mol Cell Biochem. 1996 Feb 9;155(1):77-83.
Pubmed: 8717442
- Cunnane SC, Hamadeh MJ, Liede AC, Thompson LU, Wolever TM, Jenkins DJ: Nutritional attributes of traditional flaxseed in healthy young adults. Am J Clin Nutr. 1995 Jan;61(1):62-8.
Pubmed: 7825540
- 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.
Pubmed: 16249438
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| Enzymes |
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| Name: |
Cytosolic phospholipase A2
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| Reactions: |
- 2-lysophosphatidylcholine + H2O = glycerophosphocholine + a carboxylate [RN:R07291]
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| Gene Name: |
PLA2G4A |
| Uniprot ID: |
P47712  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Phospholipase A2
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| Reactions: |
- phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
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| Gene Name: |
PLA2G1B |
| Uniprot ID: |
P04054  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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