Calendic acid

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Calendic acid
IUPAC name (8E,10E,12Z)-octadeca-8,10,12-trienoic acid
Other names alpha-calendic acid, 8E,10E,12Z-octadecatrienoic acid, trans-8-trans-10-cis-12-octadecatrienoic acid
Identifiers
CAS number [5204-87-5]
PubChem 5282818
SMILES CCCCC\C=C/C=C/C=C/CCCCCCC(=O)O
Properties
Molecular formula C18H30O2
Molar mass 278.43 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

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.[1]

[edit] Biosynthesis

Calendic acid is an omega-6 fatty acid.[2] 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).[3] An all-trans beta isomer has been described.[1]

[edit] Uses

Calendula flowers have been used for many centuries. Ointments or extracts are applied medicinally for reducing inflammation, wound healing, and as an antiseptic.[4] 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.[5] 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.[6]

In vitro, β-calendic acid shows anti-cancer activity against human colon cancer cells.[1]

[edit] References

Calendic acid comes from the pot marigold
Calendic acid comes from the pot marigold
  1. ^ a b c Yasui Y, Hosokawa M, Kohno H, Tanaka T, Miyashita K. "Growth inhibition and apoptosis induction by all-trans-conjugated linolenic acids on human colon cancer cells". Anticancer Res 26 (3A): 1855–60. PMID 16827117. 
  2. ^ Kinney, Tony. Metabolism in Plants to Produce Healthier Food Oils. Retrieved on 2007-01-11.
  3. ^ Christie, William W. Fatty Acids: Polyunsaturated with other than Methylene-Interrupted Double Bonds. Retrieved on 2007-01-11.
  4. ^ Cyberlipid. Polyenoic Fatty Acids. Retrieved on 2007-01-11.
  5. ^ NIH Medline Plus. MedlinePlus Herbs and Supplements: Calendula. Retrieved on 2007-11-30.
  6. ^ Powder formulation comprising conjugated octadecapolyenic acids. Retrieved on 11 January 2007.