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Linolenic Acid

PubChem CID
5280934
Structure
Linolenic Acid_small.png
Linolenic Acid_3D_Structure.png
Molecular Formula
Synonyms
  • linolenic acid
  • alpha-Linolenic acid
  • 463-40-1
  • linolenate
  • (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Molecular Weight
278.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Linolenic acid is a clear colorless liquid. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Alpha-linolenic acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect. It has a role as a micronutrient, a nutraceutical and a mouse metabolite. It is an omega-3 fatty acid and a linolenic acid. It is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate.
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.
See also: Cod Liver Oil (part of); Evening Primrose Oil (part of); Saw Palmetto (part of) ... View More ...

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Linolenic Acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

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-
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

DTOSIQBPPRVQHS-PDBXOOCHSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C18H30O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

463-40-1

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 KEGG ID

2.3.11 Lipid Maps ID (LM_ID)

2.3.12 Metabolomics Workbench ID

2.3.13 NCI Thesaurus Code

2.3.14 Nikkaji Number

2.3.15 NSC Number

2.3.16 PharmGKB ID

2.3.17 Pharos Ligand ID

2.3.18 RXCUI

2.3.19 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • alpha Linolenic Acid
  • alpha Linolenic Acid, Ammonium Salt
  • alpha Linolenic Acid, Calcium Salt
  • alpha Linolenic Acid, Lithium Salt
  • alpha Linolenic Acid, Magnesium Salt
  • alpha Linolenic Acid, Potassium Salt
  • alpha Linolenic Acid, Sodium Salt
  • alpha Linolenic Acid, Zinc Salt
  • alpha-Linolenic Acid
  • alpha-Linolenic Acid, (E,E,E)-Isomer
  • alpha-Linolenic Acid, (E,E,Z)-Isomer
  • alpha-Linolenic Acid, (E,Z,E)-Isomer
  • alpha-Linolenic Acid, (E,Z,Z)-Isomer
  • alpha-Linolenic Acid, (Z,E,E)-Isomer
  • alpha-Linolenic Acid, (Z,E,Z)-Isomer
  • alpha-Linolenic Acid, (Z,Z,E)-Isomer
  • alpha-Linolenic Acid, Ammonium Salt
  • alpha-Linolenic Acid, Calcium Salt
  • alpha-Linolenic Acid, Lithium Salt
  • alpha-Linolenic Acid, Magnesium Salt
  • alpha-Linolenic Acid, Potassium Salt
  • alpha-Linolenic Acid, Sodium Salt
  • alpha-Linolenic Acid, Tin(2+) Salt
  • alpha-Linolenic Acid, Zinc Salt
  • Linolenate
  • Linolenic Acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
278.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
5.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
13
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
278.224580195 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
278.224580195 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
301
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Linolenic acid is a clear colorless liquid. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Liquid, Other Solid
Colorless liquid; [Merck Index]
Liquid

3.2.2 Boiling Point

446 °F at 17 mmHg (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
231 °C at 1.70E+01 mm Hg
PhysProp

3.2.3 Melting Point

11.7 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
-16.5 °C
PhysProp
-16.5 °C

3.2.4 Flash Point

greater than 235 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

3.2.5 Solubility

less than 1 mg/mL at 72 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
0.000124 mg/mL at 25 °C
MEYLAN,WM et al. (1996)

3.2.6 Density

0.9164 at 68 °F (NTP, 1992) - Less dense than water; will float
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

3.2.7 Vapor Pressure

0.05 mmHg at 257 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
0.00000054 [mmHg]

3.2.8 LogP

6.46
SANGSTER (1993)
6.46
SANGSTER (1993)

3.2.9 Collision Cross Section

173.8 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]
174.88 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
174.53 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

170.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

173.07 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

170.9 Ų [M+Na]+

174.6 Ų [M-H]-

173.9 Ų [M-H]-

S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

3.2.10 Kovats Retention Index

Standard non-polar
2122 , 2102 , 2120 , 2113 , 2115
Semi-standard non-polar
2158.9 , 2143 , 2154 , 2134 , 2143 , 2099 , 2162 , 2159 , 2107 , 2116 , 2116 , 2127.9
Standard polar
3292 , 3292 , 3300 , 3250

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Biological Agents -> Fatty Acids and Fats

3.4.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

3.4.2 Cosmetics

Cosmetic ingredients (Linolenic Acid) -> CIR (Cosmetic Ingredient Review)
Skin conditioning; Emollient; Hair conditioning; Cleansing; Antistatic; Surfactant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

3.4.3 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

3.4.4 Fragrances

Fragrance Ingredient (Linolenic acid) -> IFRA transparency List

3.4.5 Lipids

Lipids -> Unambiguous Lipids
Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
CDCl3
pH
Not Applic
Shifts [ppm]:Intensity
2.35:62.47, 5.36:36.18, 1.38:2.81, 1.30:18.62, 0.99:42.15, 5.37:18.74, 1.34:27.05, 5.40:11.48, 5.41:8.14, 5.33:10.60, 5.35:5.56, 2.80:25.76, 2.08:27.63, 5.38:19.56, 2.07:12.24, 5.39:11.65, 2.04:8.20, 5.32:5.21, 5.33:8.20, 1.34:27.34, 5.31:7.03, 5.34:5.44, 1.63:22.95, 5.32:6.91, 2.81:44.50, 2.36:39.11, 5.31:5.97, 5.38:12.12, 2.34:29.04, 5.42:3.28, 1.65:17.04, 2.82:27.22, 2.07:20.90, 2.82:27.05, 5.40:7.32, 0.96:59.43, 5.39:14.05, 5.41:2.11, 5.35:16.63, 5.34:9.95, 1.61:5.80, 1.66:5.80, 2.07:21.19, 0.98:100.00, 5.31:6.21, 5.32:10.83, 1.37:15.11, 2.80:24.47, 5.41:9.31, 1.30:7.55, 1.32:58.55, 5.36:19.61, 5.32:12.94, 1.62:15.69, 5.30:2.28, 2.09:16.69, 5.29:3.75, 1.38:4.57, 5.42:2.05, 1.31:40.63, 2.81:45.26, 5.36:41.80, 5.30:4.16, 5.35:16.69, 5.37:27.05, 5.39:15.69, 5.38:21.66, 2.10:4.57, 1.35:25.70, 5.36:17.74, 1.34:27.11, 1.33:30.68, 5.39:9.78, 2.06:27.28, 5.40:9.43, 2.05:27.93, 5.34:11.77
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
856010
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
CDCl3
pH
Not Applic
Shifts [ppm] (F2:F1):Intensity
5.37:128.47:0.23, 5.34:128.13:0.15, 2.08:20.58:0.02, 5.40:131.93:0.09, 1.31:29.21:1.00, 1.61:24.56:0.00, 2.34:33.95:0.48, 2.05:27.22:0.06, 5.32:127.15:0.10, 2.81:26.88:0.01, 0.94:14.27:0.09, 5.39:130.48:0.12, 2.81:25.56:0.87
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 16
View All
Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

93.0 100

95.0 85.79

91.0 71.97

108.0 66.37

107.0 48.65

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Notes
instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies
2 of 16
View All
Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

73.0 100

79.0 95.40

75.0 90.49

67.0 68.37

93.0 40.84

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Notes
instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies

4.3.2 MS-MS

1 of 6
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
N/A
Top 5 Peaks

279.0 100

280.0 17.16

261.0 16.43

149.0 10.70

123.0 6.39

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Notes
delivery=Flow_Injectionanalyzer=Triple_Quad
2 of 6
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
N/A
Top 5 Peaks

81.0 100

67.0 89.58

95.0 82.31

123.0 67.56

149.0 65.67

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Notes
delivery=Flow_Injectionanalyzer=Triple_Quad

4.3.3 LC-MS

1 of 14
View All
Authors
BGC, Helmholtz Zentrum Muenchen
Instrument
maXis plus UHR-ToF-MS, Bruker Daltonics
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
6.658 min
Precursor m/z
279.2319
Precursor Adduct
[M+H]+
Top 5 Peaks

279.2311 999

261.2196 38

243.21 24

95.0854 23

81.0694 23

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License
CC BY
2 of 14
View All
Authors
BGC, Helmholtz Zentrum Muenchen
Instrument
maXis plus UHR-ToF-MS, Bruker Daltonics
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
6.658 min
Precursor m/z
279.2319
Precursor Adduct
[M+H]+
Top 5 Peaks

81.0695 999

67.0536 791

95.0853 444

279.2305 297

109.1012 181

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License
CC BY

4.3.4 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
M+H
Precursor m/z
279.232
Instrument
Orbitrap
Ionization Mode
positive
Retention Time
CCS:
Top 5 Peaks

261.220978 100

123.116653 93.11

95.085381 79.19

109.100914 71.53

137.13208 55.60

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2 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
M+H
Precursor m/z
279.232
Instrument
Orbitrap
Ionization Mode
positive
Retention Time
CCS:
Top 5 Peaks

261.22113 100

243.210693 66.25

123.116554 51.42

95.085213 50.05

223.16922 36.41

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4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Instrument Name
Bruker IFS 85
Technique
Cell
Source of Sample
Carl Roth GmbH & Co Chem. Fabrik Karlsruhe
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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2 of 2
Technique
Crystallized film between CsI (233 K)
Source of Sample
BASF Farben & Fasern, Münster
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
PerkinElmer SpectrumTwo
Technique
ATR-IR
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Source of Sample
Aldrich
Catalog Number
856010
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
856010
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

For nutritional supplementation and for treating dietary shortage or imbalance.

7.2 FDA National Drug Code Directory

7.3 Drug Labels

Active ingredient and drug

7.4 Clinical Trials

7.4.1 ClinicalTrials.gov

7.5 Biomarker Information

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Pharmacodynamics

Alpha Linolenic Acid (ALA) is an 18-carbon polyunsaturated fatty acid with three double bonds. It is also called an omega-3 fatty acid, and is essential for all mammals. Alpha-linolenic acid (or omega 3 fatty acid) intake can decrease the risk of cardiovascular diseases by 1) preventing arrhythmias that can lead to sudden cardiac death, 2) decreasing the risk of thrombosis (blood clot formation) that can lead to heart attack or stroke, 3) decreasing serum triglyceride levels, 4) slowing the growth of atherosclerotic plaque, 5) improving vascular endothelial function, 6) lowering blood pressure slightly, and 7) decreasing inflammation. ALA deficiencies can lead to visual problems and sensory neuropathy. Scaly and hemorrhagic skin or scalp inflammations may also develop.

9.2 Mechanism of Action

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.

9.3 Human Metabolite Information

9.3.1 Tissue Locations

  • Adipose Tissue
  • Epidermis
  • Fibroblasts
  • Intestine
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle

9.3.2 Cellular Locations

  • Cytoplasm
  • Extracellular
  • Membrane

9.3.3 Metabolite Pathways

alpha-Linolenic acid metabolism

9.4 Biochemical Reactions

10 Use and Manufacturing

10.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Linolenic Acid
EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Essential fatty acid; Found in most drying oils; Used as a nutrient; [Merck Index] Used in biochemical research, drying oils, and cosmetics; [NTP]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
Industrial Processes with risk of exposure
For nutritional supplementation and for treating dietary shortage or imbalance.

10.1.1 Use Classification

EPA Safer Chemical Functional Use Classes -> Surfactants
Safer Chemical Classes -> Green circle Green circle - The chemical has been verified to be of low concern
Fragrance Ingredients
Cosmetics -> Skin conditioning; Emollient; Hair conditioning; Cleansing; Antistatic; Surfactant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

10.1.2 Industry Uses

  • Finishing agents
  • Agricultural chemicals (non-pesticidal)
  • Surface active agents
  • Lubricants and lubricant additives
  • Adhesives and sealant chemicals

10.1.3 Consumer Uses

  • Agricultural chemicals (non-pesticidal)
  • Adhesives and sealant chemicals

10.1.4 Household Products

Household & Commercial/Institutional Products

Information on 17 consumer products that contain Linolenic acid in the following categories is provided:

• Auto Products

• Personal Care

10.2 U.S. Production

Aggregated Product Volume

2019: 1,000,000 lb - <20,000,000 lb

2018: 1,000,000 lb - <20,000,000 lb

2017: 1,000,000 lb - <20,000,000 lb

2016: 1,000,000 lb - <20,000,000 lb

10.3 General Manufacturing Information

Industry Processing Sectors
  • Miscellaneous Manufacturing
  • Food, beverage, and tobacco product manufacturing
  • All Other Basic Organic Chemical Manufacturing
  • Plastics Product Manufacturing
  • Paper Manufacturing
EPA TSCA Commercial Activity Status
9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-: ACTIVE

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 87.1% (1993 of 2287) of all reports. Pictograms displayed are for 12.9% (294 of 2287) of reports that indicate hazard statements.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H317 (10.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]
Precautionary Statement Codes

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2287 reports by companies from 8 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 1993 of 2287 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 7 notifications provided by 294 of 2287 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Skin Sens. 1 (10.5%)

11.1.3 EPA Safer Chemical

Chemical: Linolenic acid

Green circle Green circle - The chemical has been verified to be of low concern based on experimental and modeled data.

11.1.4 Health Hazards

SYMPTOMS: Exposure to this compound may cause blurred vision, coughing, abdominal pain, nausea, vomiting, respiratory distress, skin burns and irritation of the skin, eyes and respiratory tract. It may also cause decreased fibrinogen levels and increased platelet adhesiveness.

ACUTE/CHRONIC HAZARDS: This compound may cause irritation of the skin, eyes and respiratory tract. It may be harmful by inhalation, ingestion or skin absorption. When heated to decomposition it may emit toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.1.5 Fire Hazards

This chemical is probably combustible. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.1.6 Hazards Summary

Oxidized by air forming peroxides that may spontaneously combust; [CAMEO] Safe when used as a flavoring agent in food; [JECFA] May cause irritation; [Sigma-Aldrich MSDS]

11.2 First Aid Measures

11.2.1 First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.3 Fire Fighting

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.4 Handling and Storage

11.4.1 Nonfire Spill Response

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, protect it from all oxidizing materials, and store it at refrigerated temperatures. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.5 Exposure Control and Personal Protection

11.5.1 Personal Protective Equipment (PPE)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.6 Stability and Reactivity

11.6.1 Air and Water Reactions

Oxidizes in air to form peroxides, which spontaneously ignite. Insoluble in water. Sensitive to heat and moisture.

11.6.2 Reactive Group

Acids, Carboxylic

Hydrocarbons, Aliphatic Unsaturated

Acids, Weak

11.6.3 Reactivity Alerts

Peroxidizable Compound

11.6.4 Reactivity Profile

LINOLENIC ACID is incompatible with bases, oxidizing agents and reducing agents. Also incompatible with peroxides, oxygen and water. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.7 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 9,12,15-Octadecatrienoic acid, (Z,Z,Z)-
New Zealand EPA Inventory of Chemical Status
9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-: Does not have an individual approval but may be used under an appropriate group standard

11.8 Other Safety Information

Chemical Assessment

IMAP assessments - 9,12,15-Octadecatrienoic acid, (Z,Z,Z)-: Human health tier I assessment

Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

12 Toxicity

12.1 Toxicological Information

12.1.1 Toxicity Summary

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.

12.1.2 Carcinogen Classification

Carcinogen Classification
Not listed by IARC.

13 Associated Disorders and Diseases

Disease
Thyroid cancer
References
Disease
Colorectal cancer
References

PubMed: 7482520, 22148915, 19006102, 23940645, 24424155, 20156336, 19678709, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Major depressive disorder
References
Disease
Essential hypertension
References
Disease
Isovaleric acidemia
References

PubMed: 15615815, 12837870, 11978597, 17850781, 19343532, 27329611, 1246461

Isovaleric acidemia: Therapeutic response to supplementation with glycine, /react-text l react-text: 82 -carnitine, or both in combination and a 10-year. follow-up case study. Molecular Genetics and Metabolism Reports. Volume 11, June 2017, Pages 2-5

MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Nature Journal References

14.6 Chemical Co-Occurrences in Literature

14.7 Chemical-Gene Co-Occurrences in Literature

14.8 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Protein Bound 3D Structures

16.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

16.2 Chemical-Target Interactions

16.3 Drug-Drug Interactions

16.4 Pathways

17 Biological Test Results

17.1 BioAssay Results

18 Taxonomy

WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
A metabolome atlas of the aging mouse brain. Nat Commun. 2021 Oct 15;12(1):6021. DOI:10.1038/s41467-021-26310-y. PMID:34654818; PMCID:PMC8519999.
The Metabolome Atlas of the Aging Mouse Brain: https://mouse.atlas.metabolomics.us

19 Classification

19.1 MeSH Tree

19.2 NCI Thesaurus Tree

19.3 ChEBI Ontology

19.4 LIPID MAPS Classification

19.5 KEGG: Metabolite

19.6 KEGG: Lipid

19.7 EPA Safer Choice

19.8 ChemIDplus

19.9 CAMEO Chemicals

19.10 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

19.11 ChEMBL Target Tree

19.12 UN GHS Classification

19.13 EPA CPDat Classification

19.14 NORMAN Suspect List Exchange Classification

19.15 CCSBase Classification

19.16 EPA DSSTox Classification

19.17 Consumer Product Information Database Classification

19.18 EPA TSCA and CDR Classification

19.19 LOTUS Tree

19.20 EPA Substance Registry Services Tree

19.21 CCS Classification - Baker Lab

19.22 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAMEO Chemicals
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    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  3. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
    9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-, dimer
    https://commonchemistry.cas.org/detail?cas_rn=29857-63-4
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. DrugBank
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    9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-
    https://www.epa.gov/chemical-data-reporting
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    9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-
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  10. European Chemicals Agency (ECHA)
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  11. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  12. Human Metabolome Database (HMDB)
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    https://ifrafragrance.org/links/copyright
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    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
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  19. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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    https://lotus.nprod.net/
  23. NCI Thesaurus (NCIt)
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  24. Toxin and Toxin Target Database (T3DB)
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  25. ChEMBL
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  26. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
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  31. Consumer Product Information Database (CPID)
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  34. DailyMed
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    https://creativecommons.org/licenses/by/4.0/
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    EPA Safer Chemical Ingredients Classification
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    https://foodb.ca/about
  41. MassBank Europe
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  43. NIST Mass Spectrometry Data Center
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    https://www.nist.gov/srd/public-law
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    http://www.nist.gov/srd/nist1a.cfm
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    https://spectrabase.com/spectrum/CafoXbjoOUC
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  56. RCSB Protein Data Bank (RCSB PDB)
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CONTENTS