9,12,15-Octadecatrienoic acid

9,12,15-Octadecatrienoic acid
Compound Structure:
Synonyms: linolenic acid;alpha-Linolenic acid;463-40-1;linolenate;(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid;a-Linolenic acid;cis,cis,cis-9,12,15-Octadecatrienoic acid;all-cis-9,12,15-Octadecatrienoic acid;(Z,Z,Z)-9,12,15-Octadecatrienoic acid;9-cis,12-cis,15-cis-
Compound ID: NMPC-514
PubChem ID:

5280934

Molecular Formula: C18H30O2
Canonical SMILES: CCC=CCC=CCC=CCCCCCCCC(=O)O
InChIKey: DTOSIQBPPRVQHS-PDBXOOCHSA-N
About the compound:

Alpha-linolenic acid (ALA) is a crucial omega-3 fatty acid found abundantly in seeds and oils, including flaxseed, hempseed, chia, and canola. As an essential nutrient, ALA cannot be produced by the human body and must be acquired through dietary means. It is vital for maintaining cardiovascular health and supporting metabolic functions. Within the body, ALA is converted into eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), though this conversion process is relatively inefficient, with men typically experiencing lower conversion rates than women[1,2,3]. Studies indicate that ALA can help reduce the risk of cardiovascular diseases by lowering levels of harmful cholesterol and triglycerides. It may also help in lowering blood pressure and possesses anti-inflammatory properties[4]. Despite its numerous health benefits, some research suggests a possible association between ALA intake and an elevated risk of prostate cancer, but these findings remain inconclusive[5]. The recommended daily intake of ALA for adults ranges from 1 to 2 grams, achievable through consumption of ALA-rich foods or supplements. However, supplements should be taken under the guidance of a healthcare provider due to potential interactions with medications, such as blood thinners[6].

References 

1. Austria, J. A., Richard, M. N., Chahine, M. N., Edel, A. L., Malcolmson, L. J., Dupasquier, C. M., & Pierce, G. N. (n.d.). Bioavailability of alpha-linolenic acid in subjects after ingestion of three different forms of flaxseed. Journal of the American College of Nutrition. Retrieved from https://www.tandfonline.com/loi/uacn20

2. Examine.com. (n.d.). Alpha-Linolenic Acid (ALA): Health benefits, dosage, and side effects. Retrieved from https://examine.com/supplements/alpha-linolenic-acid/

3. IJMS. (2023). Alpha-Linolenic Acid and Cardiovascular Events: A Narrative Review. International Journal of Molecular Sciences, 24(18). https://doi.org/10.3390/ijms241814319

4. Mount Sinai. (n.d.). Alpha-Linolenic Acid. Retrieved from https://www.mountsinai.org/health-library/supplement/alpha-linolenic-acid

5. Trumbo, P., Schlicker, S., Yates, A. A., Poos, M., & Food and Nutrition Board of the Institute of Medicine, The National Academies. (2002). Dietary reference intakes for energy, carbohydrate, fiber, fat, fatty acids, cholesterol, protein, and amino acids. Journal of the American Dietetic Association, 102(11), 1621-1630. https://doi.org/10.1016/S0002-8223(02)90346-9

6. Wikipedia. (n.d.). α-Linolenic acid. Retrieved from https://en.wikipedia.org/wiki/Alpha-linolenic_acid

GHS Hazard Statements

H317 (81.63%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H334 (17.35%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

EYES:

Remove contact lenses if the person wears them.

Flush the eyes with water or saline solution for 20-30 minutes.

Contact a hospital or poison control center immediately.

Avoid applying any substances to the eyes without a doctor's instructions.

Take the person to the hospital even if there are no obvious symptoms.

SKIN:

Wash the affected skin with water and soap.

Remove contaminated clothing and isolate it.

Call a doctor if redness or irritation occurs.

Be ready to take the person to the hospital if needed.

INHALATION:

Leave the contaminated area and breathe fresh air deeply.

Seek medical help if breathing difficulties or burning sensations occur.

Rescuers should wear proper respiratory protection.

Use Self-Contained Breathing Apparatus (SCBA) if possible; otherwise, use recommended protective gear.

INGESTION:

Don't make the person vomit.

If conscious and not convulsing, give water to dilute the substance.

Call a hospital or poison control center immediately.

Prepare to take the person to the hospital as advised.

If convulsing or unconscious, maintain an open airway and position them on their side with the head lower than the body.

Don't induce vomiting; take them to the hospital promptly.

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.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

278.4 g/mol

XLogP3

5.9

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

2

Rotatable Bond Count

13

Exact Mass

278.224580195 g/mol

Monoisotopic Mass

278.224580195 g/mol

Topological Polar Surface Area

37.3Ų

Heavy Atom Count

20

Formal Charge

0

Complexity

301

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

3

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Linolenic acid is a clear colorless liquid. (NTP, 1992)

Boiling Point

446 °F at 17 mmHg (NTP, 1992)

Meting Point

11.7 °F (NTP, 1992)

Density

0.9164 at 68 °F (NTP, 1992)

Solubility 

less than 1 mg/mL at 72 °F (NTP, 1992)

Vapor Pressure

0.05 mmHg at 257 °F (NTP, 1992)

Source: PubChem

Source Species: Acanthus montanus
Calliandra portoricensis
Phyllanthus amarus
Senecio biafrae
Tragia benthamii
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