Ζ-Carotene

ζ-Carotene
Names

IUPAC name 7,7′,8,8′-Tetrahydro-ψ,ψ-carotene
Systematic IUPAC name (6E,10E,12E,14E,16E,18E,20E,22E,26E)-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,10,12,14,16,18,20,22,26,30-undecaene
Identifiers
CAS Number	72746-33-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28068
ChemSpider	4444346
PubChem CID	5280788
UNII	341QZ5N3E6^Y
CompTox Dashboard (EPA)	DTXSID701318417
InChI InChI=1S/C40H60/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-16,19-22,25-30H,13-14,17-18,23-24,31-32H2,1-10H3/b12-11+,25-15+,26-16+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+ Key: BIWLELKAFXRPDE-WTXAYMOSSA-N InChI=1/C40H60/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-16,19-22,25-30H,13-14,17-18,23-24,31-32H2,1-10H3/b12-11+,25-15+,26-16+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+ Key: BIWLELKAFXRPDE-WTXAYMOSBK
SMILES C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(\C)CC\C=C(/C)CC\C=C(/C)C)C)C)(\CC/C=C(/CC/C=C(\C)C)C)C
Properties
Chemical formula	C₄₀H₆₀
Molar mass	540.920 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

ζ-Carotene (zeta-carotene) is a carotenoid. It is different from α-carotene and β-carotene because it is acyclic.^[1] ζ-Carotene is similar in structure to lycopene, but has an additional 4 hydrogen atoms. ζ-carotene can be used as an intermediate in forming β-carotene.^[2] A dehydrogenation reaction converts ζ-carotene into lycopene, which then can be transformed into β-carotene through the action of lycopene beta-cyclase.^[3]^[4] ζ-Carotene is a natural product found in Lonicera japonica and Rhodospirillum rubrum.

References

^ Chen Y, Li J, Fan K, Du Y, Ren Z, Xu J, Zheng J, Liu Y, Fu J, Ren D, Wang G (2017). "Mutations in the maize zeta-carotene desaturase gene lead to viviparous kernel". PLOS ONE. 12 (3): e0174270. Bibcode:2017PLoSO..1274270C. doi:10.1371/journal.pone.0174270. PMC 5365113. PMID 28339488.
^ "zeta-Carotene". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 2018-12-09.
^ Tomes ML, Quackenbush FW, Nelson OE, North B (March 1953). "The Inheritance of Carotenoid Pigment Systems in the Tomato". Genetics. 38 (2): 117–27. doi:10.1093/genetics/38.2.117. PMC 1209592. PMID 17247427.
^ Rosati C, Aquilani R, Dharmapuri S, Pallara P, Marusic C, Tavazza R, Bouvier F, Camara B, Giuliano G (November 2000). "Metabolic engineering of beta-carotene and lycopene content in tomato fruit". The Plant Journal. 24 (3): 413–9. doi:10.1046/j.1365-313x.2000.00880.x. PMID 11069713.

Carotenoids

Carotenes (C₄₀)

Xanthophylls (C₄₀)

Apocarotenoids (C_<40)

Vitamin A retinoids (C₂₀)

Retinoid drugs

Vitamins (A11)

Fat
soluble

A	α-Carotene β-Carotene Retinol^# Tretinoin^#
D	D₂ Ergosterol Ergocalciferol^# D₃ 7-Dehydrocholesterol Previtamin D₃ Cholecalciferol^# 25-hydroxycholecalciferol Calcitriol (1,25-dihydroxycholecalciferol) Calcitroic acid D₄ Dihydroergocalciferol D₅ D analogues Alfacalcidol Dihydrotachysterol Calcipotriol Tacalcitol Paricalcitol
E	Tocopherol Alpha Beta Gamma Delta Tocotrienol Alpha Beta Gamma Delta Tocofersolan
K	Naphthoquinone Phylloquinone (K₁)^# Menaquinones (K₂) Menadione (K₃)^‡ Various (K₄) 4-Amino-2-methyl-1-naphthol (K₅)^‡ 2-Methylnaphthalene-1,4-diamine (K₆) 4-Amino-3-methyl-1-naphthol (K₇)