δ-Carotene

δ-Carotene (delta-carotene) or ε,ψ-carotene is a form of carotene with an ε-ring at one end, and the other uncyclized, labelled ψ (psi). It is an intermediate synthesis product in some photosynthetic plants between lycopene and α-carotene (β,ε-carotene) or ε-carotene (ε,ε-carotene).[1] δ-Carotene is fat soluble. Delta-carotene contains an alpha-ionone instead of a beta-ionone ring;[2] this conversion is carried out by the gene Del which shifts the position of the double bond in the ring structure. The formation delta-carotene under the presence of the Del gene is sensitive to high temperatures.[3]

δ-Carotene
Skeletal formula
Space-filling model
Names
IUPAC name
ε,ψ-Carotene
Systematic IUPAC name
(6R)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E)-3,7,12,16,20,24-Hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaen-1-yl]-1,5,5-trimethylcyclohex-1-ene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C40H56/c1-32(2)18-13-21-35(5)24-15-26-36(6)25-14-22-33(3)19-11-

    12-20-34(4)23-16-27-37(7)29-30-39-38(8)28-17-31-40(39,9)10/h11-12,14-16, 18-20,22-30,39H,13,17,21,31H2,1-10H3/b12-11+,22-14+,23-16+,26-15+,

    30-29+,33-19+,34-20+,35-24+,36-25+,37-27+/t39-/m0/s1
    Key: WGIYGODPCLMGQH-GOXCNPTKSA-N
  • CC1=CCCC(C1C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C)C)C)(C)C
Properties
C40H56
Molar mass 536.873
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Cunningham FX, Gantt E (February 2001). "One ring or two? Determination of ring number in carotenoids by lycopene epsilon-cyclases". Proceedings of the National Academy of Sciences of the United States of America. 98 (5): 2905–10. doi:10.1073/pnas.051618398. PMC 30238. PMID 11226339.
  2. Tomes ML (August 1969). "Delta-carotene in the tomato". Genetics. 62 (4): 769–80. doi:10.1093/genetics/62.4.769. PMC 1212314. PMID 17248458.
  3. Tomes ML (June 1967). "The competitive effect of the Beta- and delta-carotene genes on alpha- or Beta-ionone ring formation in the tomato". Genetics. 56 (2): 227–32. doi:10.1093/genetics/56.2.227. PMC 1211498. PMID 17248383.
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