Calendic acid

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IUPACName = (8E,10E,12Z)-octadeca-8,10,12-trienoic acid
OtherNames = alpha-calendic acid, 8E,10E,12Z-octadecatrienoic acid, trans-8-trans-10-cis-12-octadecatrienoic acid
Section1 = Chembox Identifiers
CASNo = 5204-87-5
PubChem = 5282818
SMILES = CCCCCC=C/C=C/C=C/CCCCCCC(=O)O
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Formula = C₁₈H₃₀O₂
MolarMass = 278.43 g/mol
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Calendic acid (sometimes α-Calendic acid) is an unsaturated fatty acid, named for the pot marigold (genus "Calendula"), from which it is obtained. It is chemically similar to the conjugated linoleic acids; laboratory work suggests it may have similar health benefits.cite journal |author=Yasui Y, Hosokawa M, Kohno H, Tanaka T, Miyashita K |title=Growth inhibition and apoptosis induction by all-trans-conjugated linolenic acids on human colon cancer cells |journal=Anticancer Res |volume=26 |issue=3A |pages=1855–60 |year= |pmid=16827117]

Biosynthesis

Calendic acid is an omega-6 fatty acid.cite web
author = Kinney, Tony
title= Metabolism in Plants to Produce Healthier Food Oils
url= http://www.metabolicengineering.gov/me2005/Kinney.pdf
accessdate= 2007-01-11|format=PDF] though not usually listed with this group.Calendic acid (8t,10t,12c-18:3) is synthesised in "Calendula officinalis" from linoleate (9c,12c-18:2) by an unusual Δ12-oleate desaturase (a FAD 2 variant) that converts the cis-double bond in position 9 to a trans,trans-conjugated double bond system (8t,10t).cite web|publisher=Lipid Library|title=Fatty Acids: Polyunsaturated with other than Methylene-Interrupted Double Bonds |url=http://www.lipidlibrary.co.uk/Lipids/fa_conj+/index.htm|author= Christie, William W| accessdate= 2007-01-11] An "all-trans" beta isomer has been described.

Uses

Calendula flowers have been used for many centuries. Ointments or extracts are applied medicinally for reducing inflammation, wound healing, and as an antiseptic. [cite web|author=Cyberlipid|url= http://www.cyberlipid.org/fa/acid0003.htm| accessdate= 2007-01-11|title=Polyenoic Fatty Acids] The US National Institute of Health's MedlinePlus states that there is 'B' grade evidence ('good scientific evidence') for the efficacy of topical use of Calendula in protecting the skin of patients undergoing radiation treatments.cite web
author = NIH Medline Plus
url=http://www.nlm.nih.gov/medlineplus/druginfo/natural/patient-calendula.html
title=MedlinePlus Herbs and Supplements: Calendula
accessdate= 2007-11-30] It assigns a 'C' grade (Unclear scientific evidence) for uses in ear infection, skin inflammation and wound and burn healing.

Calendic acid is the fatty acid responsible for the reduction in feed intake and improved feed utilization in mice when calendular oil is added to the feedstuff, as demonstrated by the comparative experiments in the examples using corn oil. [http://www.freshpatents.com/Powder-formulation-comprising-conjugated-octadecapolyenic-acids-dt20050602ptan20050118208.php?type=description Powder formulation comprising conjugated octadecapolyenic acids.] Retrieved on 11 January 2007.]

In vitro, β-calendic acid shows anti-cancer activity against human colon cancer cells.

References