470-38-2

Basic information

• Product Name: (3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione
• Synonyms: (3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione;(3S,3'S,5R,5'R)-3,3'-Dihydroxy-κ,κ-carotene-6,6'-dione;Epiisocapsorubin
• CAS NO: 470-38-2
• Molecular Formula: C₄₀H₅₆O₄
• Molecular Weight: 600.87024
• EINECS: 207-425-2
• Product Categories: Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 470-38-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 201 °C
• Boiling Point: 741.8°Cat760mmHg
• Flash Point: 416.4°C
• Appearance: /
• Density: 1.016g/cm³
• PKA: 14.55±0.60(Predicted)
• CAS DataBase Reference: (3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione(470-38-2)
• EPA Substance Registry System: (3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione(470-38-2)

Safety Data

• Hazardous Substances Data: 470-38-2(Hazardous Substances Data)

Usage

Uses

Capsorubin, is a carotenoid pigment. It is also a metabolite of a Xanthophyll (X742000) with a structure containing unusual five-membered ring end groups. It is found in red peppers (Capsicum annuum), which has shown to have Antioxidant, Antinociceptive, and Anti-inflammatory effects.

Purification Methods

Possible impurities are zeaxanthin and capsanthin. Purify capsorubin by chromatography on a column of CaCO3 or MgO. Crystallise it from *benzene/pet ether or CS2. [Beilstein 1

Upstream product

• 60497-67-8 (2E,4E,6E,8Z,10E,12E,14E,16E,18E)-1,20-Bis-((1R,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl)-4,8,13,17-tetramethyl-icosa-2,4,6,8,10,12,14,16,18-nonaene-1,20-dione 
• 336105-82-9 (2E,4E,6E,8E,10E,12E)-14[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-2,7,11-trimethyl-14-oxotetradeca-2,4,6,8,10,12-hexaenal 
• 89155-87-3 Methyl <(R)-1,2,2-trimethyl-3-cyclopenten-1-yl>keton 
• 54812-06-5 (1R)-1,2,2-trimethylcyclopent-3-ene-1-carboxylic acid 
• 54200-35-0 methyl (-)-(1S,4R)-camphanoate 
• 87859-84-5 (-)-(1R,3R)-3-chlorocamphoric anhydride 
• 502-70-5 crocetindial 
• 65243-75-6 cis-3-acetyl-3,4,4-trimethylcyclopentan-1-ol 
• 65243-75-6 trans-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)ethanone 
• 65243-75-6 <(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon 
• 65243-74-5 cis-3-methoxycarbonyl-3,4,4-trimethylcyclopentan-1-ol 
• 871882-82-5 4-Hydroxy-1,2,2-trimethyl-cyclopentanecarboxylic acid methyl ester 
• 54812-10-1 cis-4-hydroxy-1,2,2-trimethylcyclopentanecarboxylic acid 
• 54812-10-1 trans-4-hydroxy-1,2,2-trimethylcyclopentanecarboxylic acid 

Relevant articles and documents

Total synthesis of capsanthin and capsorubin using Lewis acid-promoted regio- and stereoselective rearrangement of tetrasubsutituted epoxides

The synthesis of capsanthin 1 and capsorubin 2 was accomplished via the C15-cyclopentyl ketone 6 prepared by Lewis acid-promoted regio- and stereoselective rearrangement of the epoxy dienal 5. The Royal Society of Chemistry.

Carotenoids and Related Compounds. Part 37. Stereochemistry and Synthesis of Capsorubin

The two oxygen substitutents in the end groups of capsorubin were shown to be trans to one another by synthesis of optically inactive forms of the carotenoid, and of the isomers which have the corresponding cis-structure.The 3S,5R,3'S,5'R configuration thus established for the natural carotenoid was confirmed by synthesis of this stereoisomer from (+)-camphor.Cryptocapsin has the 3'S,5'R configuration, and the racemic form has been synthesised.Capsanthin has the 3R,3'S,5'R configuration.