Dehydroretinal

Dehydroretinal
Skeletal formula of dehydroretinal
Ball-and-stick model of the dehydroretinal molecule
Names
IUPAC name
3,4-Didehydroretinal
Systematic IUPAC name
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraenal
Other names
3,4-Dehydroretinal; 3,4-Didehydroretinaldehyde
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChemSpider
ECHA InfoCard 100.006.781 Edit this at Wikidata
EC Number
  • 207-457-7
KEGG
MeSH Dehydroretinal
UNII
  • InChI=1S/C20H26O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6-13,15H,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
    Key: QHNVWXUULMZJKD-OVSJKPMPSA-N
  • InChI=1/C20H26O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6-13,15H,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
    Key: QHNVWXUULMZJKD-OVSJKPMPBA
  • O=C\C=C(\C=C\C=C(\C=C\C1=C(\C=C/CC1(C)C)C)C)C
Properties
C20H26O
Molar mass 282.427 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dehydroretinal (3,4-dehydroretinal) is a derivative metabolite of retinal[1] belonging to the group of vitamin A2 as a retinaldehyde form, besides the endogenously present 3,4-dehydroretinol and 3,4-dehydroretinoic acid.[2][3]

The livers of some freshwater fishes and some fish found in India contain a higher ratio of dehydroretinal to retinal than do other species.[4][5]

  1. ^ Gibney, Michael J.; Margetts, Barrie M.; Kearney, John M.; et al., eds. (2012), Public Health Nutrition, John Wiley & Sons, p. 210, ISBN 978-1118574225
  2. ^ Törmä H, Vahlquist A (1985). "Biosynthesis of 3-dehydroretinol (vitamin A2) from all-trans-retinol (vitamin A1) in human epidermis". J. Invest. Dermatol. 85 (6): 498–500. doi:10.1111/1523-1747.ep12277290. PMID 4067325.
  3. ^ Vahlquist A (1980). "The identification of dehydroretinol (vitamin A2) in human skin". Experientia. 36 (3): 317–318. doi:10.1007/bf01952299. PMID 7371787. S2CID 31357743.
  4. ^ MortonRA, Stubbs AL (1946). "Ling cod and other fish liver oils rich in vitamin A2". Biochem J. 40 (5–6): lix. PMID 20277273.
  5. ^ Food and Agriculture Organization of the United Nations (1967), Requirements of Vitamin A, Thiamine, Riboflavin & Niacin: Report of a Joint Fao-Who Expert Group, United Nations, p. 26, ISBN 9251004536