Zeinoxanthin

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Zeinoxanthin
Names
IUPAC name
(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-[(1R)-2,6,6-trimethylcyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-3-en-1-ol
Other names
Physoxanthin, 3-Hydroxy-alpha-carotene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-26,36-37,41H,15,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-,37+/m1/s1
    Key: NBZANZVJRKXVBH-NHWXEJKLSA-N
  • CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2C(=CCCC2(C)C)C)C)C
Properties
C40H56O
Molar mass 552.887 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Zeinoxanthin is a rare carotenoid[1] with antioxidant properties, commonly found in foods like oranges[2] and also present in the tissues of the human eye.

The word "zeinoxanthin" comes from the Greek words "zeinos", which means "grain", and "xanthus", which means "yellow". The name indicates the presence of this pigment in plants such as corn, in which it can be found.[3]

The compound is closely associated with zeaxanthin and shares comparable antioxidant benefits, playing a role in supporting eye health and shielding against oxidative damage.

Natural occurrence

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Zeaxanthin is a yellow pigment found in leafy plants and egg yolks.[4] The compound belongs to the group of xanthines and is found in various plant sources, such as Aplysia, Blechnum, Capsicum,[5] Cladonia, Diospyros, and many others.

Isolation

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A crystalline carotenoid zeinoxanthin was identified and isolated from yellow maize kernels. The compound was purified from corn gluten through a multi-step process involving solvent extraction, chromatographic separation, and sequential crystallization in benzene-methanol solvent systems.[6]

Uses

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Zeinoxanthin is used in the lutein biosynthesis.[7][8]

The reaction known to consume the compound:

zeinoxanthin + reduced [NADPH-hemoprotein reductase] + dioxygen → lutein + oxidized [NADPH-hemoprotein reductase] + H2O[9]

References

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  1. ^ Loeber, D. E.; Russell, S. W.; Toube, T. P.; Weedon, B. C. L.; Diment, J. (1 January 1971). "Carotenoids and related compounds. Part XXVIII. Synthesis of zeaxanthin, β-cryptoxanthin, and zeinoxanthin (α-cryptoxanthin)". Journal of the Chemical Society C: Organic: 404–408. doi:10.1039/J39710000404. ISSN 0022-4952. Retrieved 12 April 2025.
  2. ^ Meléndez-Martínez, Antonio J.; Britton, George; Vicario, Isabel M.; Heredia, Francisco J. (1 August 2005). "Identification of Zeinoxanthin in Orange Juices". Journal of Agricultural and Food Chemistry. 53 (16): 6362–6367. Bibcode:2005JAFC...53.6362M. doi:10.1021/jf050370c. ISSN 0021-8561. PMID 16076119. Retrieved 12 April 2025.
  3. ^ Gross, Jeana (6 December 2012). Pigments in Vegetables: Chlorophylls and Carotenoids. Springer Science & Business Media. p. 139. ISBN 978-1-4615-2033-7. Retrieved 12 April 2025.
  4. ^ Handelman, G. J.; Nightingale, Z. D.; Lichtenstein, A. H.; Schaefer, E. J.; Blumberg, J. B. (August 1999). "Lutein and zeaxanthin concentrations in plasma after dietary supplementation with egg yolk". The American Journal of Clinical Nutrition. 70 (2): 247–251. doi:10.1093/ajcn.70.2.247. ISSN 0002-9165. PMID 10426702.
  5. ^ Minguez-Mosquera, M. Isabel; Hornero-Mendez, Damaso (1 October 1993). "Separation and quantification of the carotenoid pigments in red peppers (Capsicum annuum L.), paprika, and oleoresin by reversed-phase HPLC". Journal of Agricultural and Food Chemistry. 41 (10): 1616–1620. Bibcode:1993JAFC...41.1616M. doi:10.1021/jf00034a018. ISSN 0021-8561. Retrieved 12 April 2025.
  6. ^ Petzold, E. N.; Quackenbush, F. W. (1 February 1960). "Zeinoxanthin, a crystalline carotenol from corn gluten". Archives of Biochemistry and Biophysics. 86 (2): 163–165. doi:10.1016/0003-9861(60)90396-9. ISSN 0003-9861. PMID 14432452. Retrieved 12 April 2025.
  7. ^ "MetaCyc zeinoxanthin". vm-trypanocyc.toulouse.inra.fr. Retrieved 12 April 2025.
  8. ^ Kim, Joonyul; DellaPenna, Dean (28 February 2006). "Defining the primary route for lutein synthesis in plants: The role of Arabidopsis carotenoid β-ring hydroxylase CYP97A3". Proceedings of the National Academy of Sciences. 103 (9): 3474–3479. Bibcode:2006PNAS..103.3474K. doi:10.1073/pnas.0511207103. PMC 1413914. PMID 16492736.
  9. ^ "MetaCyc zeinoxanthin". solcyc.sgn.cornell.edu. Retrieved 13 April 2025.