(3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione

Base Information

• Chemical Name: (3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione
• CAS No.: 470-38-2
• Molecular Formula: C40H56 O4
• Molecular Weight: 600.882
• Mol file: 470-38-2.mol

Synonyms:2,4,6,8,10,12,14,16,18-Eicosanonaene-1,20-dione,1,20-bis(4-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethyl-,(1R,1R,4S,4S)-(all-E)- (8CI); Capsorubin; Capsorubin, all-trans-;all-trans-Capsorubin

Chemical Property of (3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione

Chemical Property:

• Melting Point: 201 °C
• Boiling Point: 741.8°Cat760mmHg
• PKA: 14.55±0.60(Predicted)
• Flash Point: 416.4°C
• PSA: 74.60000
• Density: 1.016g/cm³
• LogP: 9.06520

Purity/Quality:

99%, ^*data from raw suppliers

Capsorubin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• 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.

Technology Process of (3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione

There total 62 articles about (3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 30.0%

C33H38O2P(1+)*Cl(1-) + (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 (336105-82-9) → capsorubin (470-38-2)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1039/b710386g

Reference yield:

(R)-1,2,2-trimethyl-cyclopent-3-ene-1,3-dicarboxylic acid (87798-58-1) → capsorubin (470-38-2)

Guidance literature:

Multi-step reaction with 8 steps

1: lithium bromide, hydrobromic acid / 100 °C

2: 55 percent / aq. sodium carbonate / Heating

4: 95 percent / 2N-sodium hydroxide / 1.5 h / Heating

5: 1.) 0.5N-hydrochloric acid, hydrogen / 1.)platinum dioxide / 1.) glacial acetic acid, 20 deg C, 30 h, 2.) ether

6: 7 mg / 2N sodium hydroxide / 2 h / Heating

7: 55 percent / diethyl ether / 18 h / Heating

8: potassium hydroxide / ethanol / 1.) 40 deg C, 5 min, 2.) in dark, 68 h

With hydrogenchloride; potassium hydroxide; sodium hydroxide; hydrogen bromide; hydrogen; sodium carbonate; lithium bromide; platinum(IV) oxide; In diethyl ether; ethanol;

Reference yield:

D-(+)-camphoric acid (124-83-4) → capsorubin (470-38-2)

Guidance literature:

Multi-step reaction with 17 steps

1: 83 percent / phosphorus pentachloride

2: 85 percent / ice, water / dimethylformamide

3: 87 percent / 0.1N-sulphuric acid / Heating

4: 91 percent / sulphuric acid

5: 90 percent / lithium aluminium hydride / diethyl ether / 18 h / Heating

6: periodic acid / H₂O / 1 h / 20 °C

7: 82 percent / potassium hydroxide / ethanol; H₂O / 1.) reflux, 30 min, 2.) 20 deg C, 18 h

8: 95 percent / sodium borohydride, sodium hydroxide / methanol / 24 h / 20 °C

9: 98 percent / pyridine / 18 h / 20 °C

10: 1.) ozone, oxygen, 2.) acetic acid, zinc / 1.) methanol, -70 deg C, 80 min, 2.) 0 deg C

11: 85 percent / zinc, glacial acetic acid / 18 h / Heating

12: 86 percent / potassium hydroxide / methanol / 18 h / 20 °C

13: 97 percent / CrO₃, H₂O, H₂SO₄ / acetone / 0.5 h / 20 °C

14: 1.) 0.5N-hydrochloric acid, hydrogen / 1.)platinum dioxide / 1.) glacial acetic acid, 20 deg C, 30 h, 2.) ether

15: 7 mg / 2N sodium hydroxide / 2 h / Heating

16: 55 percent / diethyl ether / 18 h / Heating

17: potassium hydroxide / ethanol / 1.) 40 deg C, 5 min, 2.) in dark, 68 h

With pyridine; chromium(VI) oxide; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; phosphorus pentachloride; sulfuric acid; Methamphetamin; water; hydrogen; oxygen; ozone; acetic acid; periodic acid; zinc; platinum(IV) oxide; In methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetone;

upstream raw materials:

crocetindial

<(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon

(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

(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

Refernces

• 1、 Molnar, Peter,Kortvelyesi, Tarnas,Matus, Zoltan,Szabolca, Jozsef. "Kinetic Studies on the Thermal (Z/E)-Isomerization of C40-Carotenoids". . p. 801 - 841. Retrieved 2007/10/03.
• 2、 Ruttimann,Engbert,Mayer,et al.. "Synthesis of optically active natural carotenoids and structurally related compounds. X. Synthesis of (3R,3'S,5'R)-capsanthin, 3S,5R,3'S,5'R)-capsorubin, (3'S,5'R)-cryptocapsin, and some related compounds. A new approach to optically active, five-membered-ring carotenoid building units by hydroboration". . p. 1939 - 1960. Retrieved 2007/10/02.