Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:27 UTC
HMDB IDHMDB01388
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlpha-Linolenic acid
DescriptionAlpha-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
Thumb
Synonyms
  1. (9,12,15)-linolenate
  2. (9,12,15)-linolenic acid
  3. (9Z,12Z,15Z)-Octadecatrienoate
  4. (9Z,12Z,15Z)-Octadecatrienoic acid
  5. (Z,Z,Z)-9,12,15-Octadecatrienoate
  6. (Z,Z,Z)-9,12,15-Octadecatrienoic acid
  7. 9,12,15-Octadecatrienoate
  8. 9,12,15-Octadecatrienoic acid
  9. 9-cis,12-cis,15-cis-Octadecatrienoate
  10. 9-cis,12-cis,15-cis-Octadecatrienoic acid
  11. a-Linolenate
  12. a-Linolenic acid
  13. All-cis-9,12,15-Octadecatrienoate
  14. All-cis-9,12,15-Octadecatrienoic acid
  15. alpha-Linolenate
  16. alpha-Linolenic acid
  17. cis,cis,cis-9,12,15-Octadecatrienoate
  18. cis,cis,cis-9,12,15-Octadecatrienoic acid
  19. cis-9,12,15-Octadecatrienoate
  20. cis-9,12,15-Octadecatrienoic acid
  21. Industrene 120
  22. Linolenate
  23. Linolenic acid
Chemical FormulaC18H30O2
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
IUPAC Name(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Traditional IUPAC Nameα-linolenic acid
CAS Registry Number463-40-1
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 KeyDTOSIQBPPRVQHS-PDBXOOCHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassLineolic Acids and Derivatives
Sub ClassN/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)
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct ParentLineolic Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Cell signaling
  • Essential fatty acid
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-16.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.46SANGSTER (1993)
Predicted Properties
PropertyValueSource
water solubility2.660E-04 g/LALOGPS
logP6.62ALOGPS
logP6.06ChemAxon
logS-6ALOGPS
pKa (strongest acidic)4.99ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.3ChemAxon
rotatable bond count13ChemAxon
refractivity89.64ChemAxon
polarizability34.44ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Adipose Tissue
  • Epidermis
  • Fibroblasts
  • Intestine
  • Muscle
  • Nervous Tissues
  • Placenta
  • Platelet
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018map00592
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified5.11 +/- 3.8 uMAdult (>18 years old)Not SpecifiedNormal
BloodDetected and Quantified17.5 +/- 7.6 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified16.8 +/- 7.3 uMAdult (>18 years old)MaleNormal
BloodDetected and Quantified18.5 +/- 7.9 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified1.1 +/- 0.8 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified1.975 +/- 1.223 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.115 +/- 0.004 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.73 +/- 0.54 umol/mmol creatinineAdult (>18 years old)FemaleNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified21.2 +/- 7.2 uMAdult (>18 years old)BothHypertension
BloodDetected and Quantified20.5 +/- 7.5 uMAdult (>18 years old)MaleEssential hypertension
BloodDetected and Quantified22.7 +/- 6.2 uMAdult (>18 years old)FemaleEssential hypertension
UrineDetected and Quantified0.49 +/- 0.46 umol/mmol creatinineAdult (>18 years old)FemaleCancer
Associated Disorders and Diseases
Disease References
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
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
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
Associated OMIM IDs
DrugBank IDDB00132
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012462
KNApSAcK IDC00007247
Chemspider ID4444437
KEGG Compound IDC06427
BioCyc IDLINOLENIC_ACID
BiGG ID48237
Wikipedia LinkLinolenic acid
NuGOwiki LinkHMDB01388
Metagene LinkHMDB01388
METLIN ID6208
PubChem Compound5280934
PDB IDLNL
ChEBI ID27432
References
Synthesis ReferenceLi, 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
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. 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
  17. Connor WE: Importance of n-3 fatty acids in health and disease. Am J Clin Nutr. 2000 Jan;71(1 Suppl):171S-5S. Pubmed: 10617967
  18. Lauritzen I, Blondeau N, Heurteaux C, Widmann C, Romey G, Lazdunski M: Polyunsaturated fatty acids are potent neuroprotectors. EMBO J. 2000 Apr 17;19(8):1784-93. Pubmed: 10775263
  19. Cho E, Hung S, Willett WC, Spiegelman D, Rimm EB, Seddon JM, Colditz GA, Hankinson SE: Prospective study of dietary fat and the risk of age-related macular degeneration. Am J Clin Nutr. 2001 Feb;73(2):209-18. Pubmed: 11157315
  20. Kris-Etherton PM, Harris WS, Appel LJ: Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation. 2002 Nov 19;106(21):2747-57. Pubmed: 12438303
  21. Brouwer IA, Katan MB, Zock PL: Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis. J Nutr. 2004 Apr;134(4):919-22. Pubmed: 15051847

Enzymes

Gene Name:
PLA2G5
Uniprot ID:
P39877
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G10
Uniprot ID:
O15496
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G6
Uniprot ID:
O60733
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G2A
Uniprot ID:
P14555
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G4C
Uniprot ID:
Q9UP65
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G3
Uniprot ID:
Q9NZ20
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
ACOT7
Uniprot ID:
O00154
Reactions
Alpha-Linolenoyl-CoA + Water unknown Coenzyme A + Alpha-Linolenic aciddetails
Gene Name:
ACOT2
Uniprot ID:
P49753
Reactions
Alpha-Linolenoyl-CoA + Water unknown Coenzyme A + Alpha-Linolenic aciddetails
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Reactions
Alpha-Linolenoyl-CoA + Water unknown Coenzyme A + Alpha-Linolenic aciddetails
Gene Name:
ACOT8
Uniprot ID:
O14734
Gene Name:
FADS1
Uniprot ID:
O60427
Gene Name:
SLC8A1
Uniprot ID:
P32418
Gene Name:
FADS2
Uniprot ID:
O95864
Gene Name:
PLB1
Uniprot ID:
Q6P1J6
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G4D
Uniprot ID:
Q86XP0
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G4E
Uniprot ID:
Q3MJ16
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G4F
Uniprot ID:
Q68DD2
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
PLA2G4B
Uniprot ID:
P0C869
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Gene Name:
ACOT1
Uniprot ID:
Q86TX2
Reactions
Alpha-Linolenoyl-CoA + Water unknown Coenzyme A + Alpha-Linolenic aciddetails
Gene Name:
PLA2G16
Uniprot ID:
P53816
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails
Phosphatidylcholine + Water unknown 2-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic aciddetails