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Calendic acid

From Wikipedia, the free encyclopedia
Fatty acid
Calendic acid
Names
Preferred IUPAC name
(8E,10E,12Z)-Octadeca-8,10,12-trienoic acid
Other names
  • α-Calendic acid
  • (8E,10E,12Z)-Octadecatrienoic acid
  • trans-8-trans-10-cis-12-Octadecatrienoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-11H,2-5,12-17H2,1H3,(H,19,20)/b7-6-,9-8+,11-10+ checkY
    Key: DQGMPXYVZZCNDQ-KBPWROHVSA-N checkY
  • InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-11H,2-5,12-17H2,1H3,(H,19,20)/b7-6-,9-8+,11-10+
    Key: DQGMPXYVZZCNDQ-KBPWROHVBR
  • O=C(O)CCCCCC\C=C\C=C\C=C/CCCCC
Properties
C18H30O2
Molar mass278.436 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Calendic acid (sometimesα-calendic acid) is anunsaturated fatty acid, named for thepot marigold (Calendula officinalis), from which it is obtained. It is chemically similar to theconjugated linoleic acids; laboratory work suggests it may have similarin vitro bioactivities.[1]

Biosynthesis

[edit]

Calendic acid is anomega-6 fatty acid.[2] though not usually listed with this group. Calendic acid is synthesised inCalendula officinalis fromlinoleate by an unusual Δ12-oleatedesaturase (a FAD 2 variant) that converts thecis-double bond at position 9 to atrans,trans-conjugated double bond system.[3] Anall-trans beta isomer has been described.[1]

Calendic acid comes from the pot marigold

Effects

[edit]

Calendic acid is the fatty acid responsible for the reduction in feed intake and improved feed utilization in mice when calendula oil is added to the feedstuff, as demonstrated by the comparative experiments in the examples using corn oil.[4]

References

[edit]
  1. ^abYasui Y, Hosokawa M, Kohno H, Tanaka T, Miyashita K (2006). "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"(PDF). Archived fromthe original(PDF) on 2006-09-29. Retrieved2007-01-11.
  3. ^Christie, William W."Fatty Acids: Polyunsaturated with other than Methylene-Interrupted Double Bonds". Lipid Library. Archived fromthe original on 2007-01-12. Retrieved2007-01-11.
  4. ^US Patent 20050118208: Powder formulation comprising conjugated octadecapolyenic acids
Saturated
ω−3 Unsaturated
ω−5 Unsaturated
ω−6 Unsaturated
ω−7 Unsaturated
ω−9 Unsaturated
ω−10 Unsaturated
ω−11 Unsaturated
ω−12 Unsaturated
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