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MedKoo Cat#: 573712 | Name: Capsanthin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Capsanthin is a carotenoid found in red paprika that has diverse biological activities. It reduces hydrogen peroxide-induced production of reactive oxygen species (ROS) and phosphorylation of ERK and p38 and prevents inhibition of gap-junction intracellular communication in WB-F344 rat liver epithelial cells. Capsanthin reduces the number of colonic aberrant crypt foci and preneoplastic lesions in a rat model of N-methylnitrosourea-induced colon carcinogenesis. It also reduces ear edema in a mouse model of inflammation induced by phorbol 12-myristate 13-acetate.

Chemical Structure

Capsanthin
Capsanthin
CAS#465-42-9

Theoretical Analysis

MedKoo Cat#: 573712

Name: Capsanthin

CAS#: 465-42-9

Chemical Formula: C40H56O3

Exact Mass: 584.4229

Molecular Weight: 584.89

Elemental Analysis: C, 82.14; H, 9.65; O, 8.21

Price and Availability

Size Price Availability Quantity
1mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
all-trans-Capsanthin, all trans Capsanthin, Capsanthin, capsorubin, Paprika extract
IUPAC/Chemical Name
(2E,4E,6E,8E,10E,12E,14E,16E,18E)-1-((1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl)-19-((R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
InChi Key
VYIRVAXUEZSDNC-RDJLEWNRSA-N
InChi Code
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
SMILES Code
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
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 584.89 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kennedy LE, Abraham A, Kulkarni G, Shettigar N, Dave T, Kulkarni M. Capsanthin, a Plant-Derived Xanthophyll: a Review of Pharmacology and Delivery Strategies. AAPS PharmSciTech. 2021 Jul 9;22(5):203. doi: 10.1208/s12249-021-02065-z. PMID: 34244867. 2: Kim S, Lee YR, Lee EO, Jin H, Choi YH, Joo HK, Jeon BH. Capsanthin Inhibits Atherosclerotic Plaque Formation and Vascular Inflammation in ApoE-/- Mice. Biomedicines. 2022 Jul 23;10(8):1780. doi: 10.3390/biomedicines10081780. PMID: 35892680; PMCID: PMC9332034. 3: Shanmugham V, Subban R. Capsanthin-Loaded Micelles: Preparation, Characterization and in vitro Evaluation of Cytotoxicity Using MDA-MB-231 Breast Cancer Cell Line. Food Technol Biotechnol. 2022 Sep;60(3):350-360. doi: 10.17113/ftb.60.03.22.7405. PMID: 36320357; PMCID: PMC9590259. 4: Erden Y. Capsanthin Stimulates the Mitochondrial Apoptosis-Mediated Cell Death, following DNA Damage in MCF-7 Cells. Nutr Cancer. 2021;73(4):662-670. doi: 10.1080/01635581.2020.1819347. Epub 2020 Sep 16. PMID: 32933334. 5: Furubayashi M, Kubo A, Takemura M, Otani Y, Maoka T, Terada Y, Yaoi K, Ohdan K, Misawa N, Mitani Y. Capsanthin Production in Escherichia coli by Overexpression of Capsanthin/Capsorubin Synthase from Capsicum annuum. J Agric Food Chem. 2021 May 5;69(17):5076-5085. doi: 10.1021/acs.jafc.1c00083. Epub 2021 Apr 23. PMID: 33890772. 6: Wu JY, Chien YC, Tsai IC, Hung CC, Huang WC, Liu LC, Yu YL. Capsanthin induces G1/S phase arrest, erlotinib-sensitivity and inhibits tumor progression by suppressing EZH2-mediated epigenetically silencing of p21 in triple-negative breast cancer cells. Aging (Albany NY). 2021 May 2;13(9):12514-12525. doi: 10.18632/aging.202925. Epub 2021 May 2. PMID: 33934088; PMCID: PMC8148495. 7: Kulkarni M, Goge N, Date AA. Development of Nanoemulsion Preconcentrate of Capsanthin with Improved Chemical Stability. Assay Drug Dev Technol. 2020 Jan;18(1):34-44. doi: 10.1089/adt.2019.916. Epub 2019 Sep 6. PMID: 31502853; PMCID: PMC6998047. 8: Joo HK, Lee YR, Lee EO, Kim S, Jin H, Kim S, Lim YP, An CG, Jeon BH. Protective Role of Dietary Capsanthin in a Mouse Model of Nonalcoholic Fatty Liver Disease. J Med Food. 2021 Jun;24(6):635-644. doi: 10.1089/jmf.2020.4866. PMID: 34161164. 9: Shanmugham V, Subban R. Capsanthin from Capsicum annum fruits exerts anti- glaucoma, antioxidant, anti-inflammatory activity, and corneal pro-inflammatory cytokine gene expression in a benzalkonium chloride-induced rat dry eye model. J Food Biochem. 2022 Oct;46(10):e14352. doi: 10.1111/jfbc.14352. Epub 2022 Jul 27. PMID: 35892258. 10: Saini RK, Prasad P, Lokesh V, Shang X, Shin J, Keum YS, Lee JH. Carotenoids: Dietary Sources, Extraction, Encapsulation, Bioavailability, and Health Benefits-A Review of Recent Advancements. Antioxidants (Basel). 2022 Apr 18;11(4):795. doi: 10.3390/antiox11040795. PMID: 35453480; PMCID: PMC9025559. 11: Maeda H, Nishino A, Maoka T. Biological Activities of Paprika Carotenoids, Capsanthin and Capsorubin. Adv Exp Med Biol. 2021;1261:285-293. doi: 10.1007/978-981-15-7360-6_26. PMID: 33783751. 12: Jo SJ, Kim JW, Choi HO, Kim JH, Kim HJ, Woo SH, Han BH. Capsanthin Inhibits both Adipogenesis in 3T3-L1 Preadipocytes and Weight Gain in High-Fat Diet- Induced Obese Mice. Biomol Ther (Seoul). 2017 May 1;25(3):329-336. doi: 10.4062/biomolther.2017.048. PMID: 28449555; PMCID: PMC5424644. 13: Langi P, Kiokias S, Varzakas T, Proestos C. Carotenoids: From Plants to Food and Feed Industries. Methods Mol Biol. 2018;1852:57-71. doi: 10.1007/978-1-4939-8742-9_3. PMID: 30109624. 14: Csernus B, Szabó C, Knop R, Kidane RG, Ndunguru SF, Gulyás G, Ozsváth XE, Czeglédi L. Capsanthin supplementation modulates the immune response in broiler chickens under Escherichia coli lipopolysaccharide challenge. Arch Anim Breed. 2023 Mar 2;66(1):103-111. doi: 10.5194/aab-66-103-2023. PMID: 37312865; PMCID: PMC10258793. 15: Aizawa K, Inakuma T. Dietary capsanthin, the main carotenoid in paprika (Capsicum annuum), alters plasma high-density lipoprotein-cholesterol levels and hepatic gene expression in rats. Br J Nutr. 2009 Dec;102(12):1760-6. doi: 10.1017/S0007114509991309. PMID: 19646292. 16: Wu T, Gao Y, Hao J, Geng J, Zhang J, Yin J, Liu R, Sui W, Gong L, Zhang M. Capsanthin extract prevents obesity, reduces serum TMAO levels and modulates the gut microbiota composition in high-fat-diet induced obese C57BL/6J mice. Food Res Int. 2020 Feb;128:108774. doi: 10.1016/j.foodres.2019.108774. Epub 2019 Nov 8. PMID: 31955744. 17: Shanmugham V, Subban R. Comparison of the Anti-Obesity Effect of Enriched Capsanthin and Capsaicin from Capsicum annuum L. Fruit in Obesity-Induced C57BL/6J Mouse Model. Food Technol Biotechnol. 2022 Jun;60(2):202-212. doi: 10.17113/ftb.60.02.22.7376. PMID: 35910274; PMCID: PMC9295630. 18: Patel K, Patel DK. Biological Importance, Pharmacological Activities, and Nutraceutical Potential of Capsanthin: A Review of Capsicum Plant Capsaicinoids. Curr Drug Res Rev. 2023 Mar 31. doi: 10.2174/2589977515666230331093712. Epub ahead of print. PMID: 36999721. 19: Scholz M, Flender O, Lenzer T, Oum K. Ultrafast Excited-State Dynamics of all-trans-Capsanthin in Organic Solvents. J Phys Chem A. 2017 Nov 9;121(44):8380-8388. doi: 10.1021/acs.jpca.7b08252. Epub 2017 Nov 1. PMID: 29090578. 20: Nishino A, Yasui H, Maoka T. Reaction of Paprika Carotenoids, Capsanthin and Capsorubin, with Reactive Oxygen Species. J Agric Food Chem. 2016 Jun 15;64(23):4786-92. doi: 10.1021/acs.jafc.6b01706. Epub 2016 Jun 3. PMID: 27229653.