Capsanthin

Capsanthin
Names
	IUPAC name (3R,3′S,5′R)-3,3′-Dihydroxy-β,κ-caroten-6′-one
	Systematic IUPAC name (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
Identifiers
CAS Number	465-42-9;
3D model (JSmol)	Interactive image;
Beilstein Reference	2493991
ChEBI	CHEBI:3375;
ChEMBL	ChEMBL1519371;
ChemSpider	4444640;
ECHA InfoCard	100.006.696
EC Number	207-364-1;
E number	E160c(i) (colours)
KEGG	C08584;
PubChem CID	5281228;
UNII	420NY1J57N;
CompTox Dashboard (EPA)	DTXSID10905012 ;
	InChI InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37(43)40(10)28-35(42)27-39(40,8)9/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t34-,35+,40+/m1/s1 Key: VYIRVAXUEZSDNC-RDJLEWNRSA-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)/C=C/C(=O)[C@@]2(C[C@H](CC2(C)C)O)C)/C)/C;
Properties
Chemical formula	C40H56O3
Molar mass	584.885 g·mol−1
Appearance	Deep red solid
Melting point	181–182 °C (358–360 °F; 454–455 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Capsanthin is a natural red dye of the xanthophyll class of carotenoids. As a food coloring, it has the E number E160c(i). Capsanthin is the main carotenoid in the Capsicum annuum species of plants including red bell pepper, New Mexico chile, and cayenne peppers (Capsicum annuum) and a component of paprika oleoresin.^[1] Capsanthin is also found in some species of lily.^[2] Of all carotenoids, capsanthin is considered to have the greatest antioxidant capacity due to the presence of eleven conjugated double bonds, a conjugated keto group, and a cyclopentane ring.^[3]^[4]

Research

Xanthophyllic carotenoids such as β-carotene, lutein, and zeaxanthin have often been touted for their ability to help eye functionality. Capsanthin may also be able to support eye health and recent research has revealed its potential to help maintain intraocular pressure within a healthy range. A clinical study on Wistar rats explored this effect over the course of 28 days. The rats were induced with higher intraocular pressure and then either given a placebo or capsanthin. At the end of the trial, rats that consumed capsanthin had normalized their eye pressure comparable to the control group that had normal pressure levels.^[5]

References

^ ^a ^b ^c Merck Index (12th ed.). p. 288. Record 1812.
^ Valadon, L. R. G.; Mummery, Rosemary S. (1977-01-01). "Carotenoids of Lilies and of Red Pepper: Biogenesis of Capsanthin and Capsorubin". Zeitschrift für Pflanzenphysiologie. 82 (5): 407–416. doi:10.1016/S0044-328X(77)80004-4. ISSN 0044-328X.
^ Hirayama, Osamu; Nakamura, Kyoko; Hamada, Syoko; Kobayasi, Yoko (February 1994). "Singlet oxygen quenching ability of naturally occurring carotenoids". Lipids. 29 (2): 149–150. doi:10.1007/BF02537155. ISSN 0024-4201. PMID 8152349. S2CID 3965039.
^ Pérez-Gálvez, Antonio; Martin, Hans D.; Sies, Helmut; Stahl, Wilhelm (June 2003). "Incorporation of carotenoids from paprika oleoresin into human chylomicrons". British Journal of Nutrition. 89 (6): 787–793. doi:10.1079/BJN2003842. ISSN 0007-1145. PMID 12828795.
^ Shanmugham, Velmurugan; Subban, Ravi (July 2021). "Extraction of capsanthin from Capsicum annum L fruits and its effect on carbomer‐induced intraocular pressure in Albino Wistar rats". Journal of Food Biochemistry. 45 (7): e13776. doi:10.1111/jfbc.13776. ISSN 0145-8884. PMID 34056744. S2CID 235255315.

[MerckIndex-1] Merck Index (12th ed.). p. 288. Record 1812.

[2] Valadon, L. R. G.; Mummery, Rosemary S. (1977-01-01). "Carotenoids of Lilies and of Red Pepper: Biogenesis of Capsanthin and Capsorubin". Zeitschrift für Pflanzenphysiologie. 82 (5): 407–416. doi:10.1016/S0044-328X(77)80004-4. ISSN 0044-328X.

[3] Hirayama, Osamu; Nakamura, Kyoko; Hamada, Syoko; Kobayasi, Yoko (February 1994). "Singlet oxygen quenching ability of naturally occurring carotenoids". Lipids. 29 (2): 149–150. doi:10.1007/BF02537155. ISSN 0024-4201. PMID 8152349. S2CID 3965039.

[4] Pérez-Gálvez, Antonio; Martin, Hans D.; Sies, Helmut; Stahl, Wilhelm (June 2003). "Incorporation of carotenoids from paprika oleoresin into human chylomicrons". British Journal of Nutrition. 89 (6): 787–793. doi:10.1079/BJN2003842. ISSN 0007-1145. PMID 12828795.

[5] Shanmugham, Velmurugan; Subban, Ravi (July 2021). "Extraction of capsanthin from Capsicum annum L fruits and its effect on carbomer‐induced intraocular pressure in Albino Wistar rats". Journal of Food Biochemistry. 45 (7): e13776. doi:10.1111/jfbc.13776. ISSN 0145-8884. PMID 34056744. S2CID 235255315.

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