meso-Zeaxanthin

*Meso*-zeaxanthin
Names
	IUPAC name (3R,3′S)-β,β-Carotene-3,3′-diol
	Systematic IUPAC name (1R)-4-{(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl}-3,5,5-trimethylcyclohex-3-en-1-ol
	Other names 3R,3′S-zeaxanthin
Identifiers
CAS Number	31272-50-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:138919;
ChemSpider	4946722;
PubChem CID	6442658;
UNII	3O63K300I5;
	InChI InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+ Key: JKQXZKUSFCKOGQ-YOPUJPICSA-N;
	SMILES CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C[C@@H](CC2(C)C)O)C)\C)\C)/C)/C;
Properties
Chemical formula	C40H56O2
Molar mass	568.87144 g/mol
Appearance	orange-red
Solubility in water	insoluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Meso-zeaxanthin (3R,3′S-zeaxanthin) is a xanthophyll carotenoid, and is one of the three stereoisomers of zeaxanthin. The meso- form is the second most abundant in nature, after 3R,3′R-zeaxanthin, which is produced by plants and algae.^[1] Meso-zeaxanthin has been identified in specific tissues of marine organisms^[2] and in the macula lutea, also known as the "yellow spot" of the human retina.^[3]^[4]

^ De Ville, T. E.; Hursthouse, M. B.; Russell, S. W.; Weedon, B. C. L. (1969). "Absolute configuration of carotenoids". Journal of the Chemical Society D: Chemical Communications. 22 (22): 1311–1312. doi:10.1039/C29690001311.
^ Maoka, Takashi; Arai, Akihiro; Shimizu, Minoru; Matsuno, Takao (1986). "The first isolation of enantiomeric and meso-zeaxanthin in nature". Comparative Biochemistry and Physiology Part B: Comparative Biochemistry. 83 (1): 121–124. doi:10.1016/0305-0491(86)90341-X. PMID 3943294.
^ Bone, R. A.; Landrum, J. T.; Friedes, L. M.; Gomez, C. M.; Kilburn, M. D.; Menendez, E.; Vidal, I.; Wang, W. (1997-02-01). "Distribution of lutein and zeaxanthin stereoisomers in the human retina". Experimental Eye Research. 64 (2): 211–218. doi:10.1006/exer.1996.0210. ISSN 0014-4835. PMID 9176055.
^ Bone, R. A.; Landrum, J. T.; Hime, G. W.; Cains, A.; Zamor, J. (1993-05-01). "Stereochemistry of the human macular carotenoids". Investigative Ophthalmology & Visual Science. 34 (6): 2033–2040. ISSN 0146-0404. PMID 8491553.

[1] De Ville, T. E.; Hursthouse, M. B.; Russell, S. W.; Weedon, B. C. L. (1969). "Absolute configuration of carotenoids". Journal of the Chemical Society D: Chemical Communications. 22 (22): 1311–1312. doi:10.1039/C29690001311.

[:0-2] Maoka, Takashi; Arai, Akihiro; Shimizu, Minoru; Matsuno, Takao (1986). "The first isolation of enantiomeric and meso-zeaxanthin in nature". Comparative Biochemistry and Physiology Part B: Comparative Biochemistry. 83 (1): 121–124. doi:10.1016/0305-0491(86)90341-X. PMID 3943294.

[:2-3] Bone, R. A.; Landrum, J. T.; Friedes, L. M.; Gomez, C. M.; Kilburn, M. D.; Menendez, E.; Vidal, I.; Wang, W. (1997-02-01). "Distribution of lutein and zeaxanthin stereoisomers in the human retina". Experimental Eye Research. 64 (2): 211–218. doi:10.1006/exer.1996.0210. ISSN 0014-4835. PMID 9176055.

[4] Bone, R. A.; Landrum, J. T.; Hime, G. W.; Cains, A.; Zamor, J. (1993-05-01). "Stereochemistry of the human macular carotenoids". Investigative Ophthalmology & Visual Science. 34 (6): 2033–2040. ISSN 0146-0404. PMID 8491553.

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