Capsanthin

Base Information

• Chemical Name: Capsanthin
• CAS No.: 465-42-9
• Deprecated CAS: 1363-22-0,113359-44-7,5957-29-9,47842-77-3
• Molecular Formula: C40H56O3
• Molecular Weight: 584.883
• Hs Code.: DERIVATION
• European Community (EC) Number: 207-364-1
• UNII: 420NY1J57N
• ChEMBL ID: CHEMBL1519371
• DSSTox Substance ID: DTXSID10905012
• Metabolomics Workbench ID: 28990
• Nikkaji Number: J5.891B
• Wikidata: Q425431
• Wikipedia: Capsanthin
• Mol file: 465-42-9.mol

Synonyms:capsanthin;capsanthin, (3R,3'S,5'R,13-cis)-isomer

Chemical Property of Capsanthin

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 2.22E-24mmHg at 25°C
• Melting Point: 177-178 °C
• Refractive Index: 1.563
• Boiling Point: 726.6 °C at 760 mmHg
• PKA: 14.85±0.60(Predicted)
• Flash Point: 407.2 °C
• PSA: 57.53000
• Density: 1.012 g/cm³
• LogP: 9.80630
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 10.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 584.42294564
• Heavy Atom Count: 43
• Complexity: 1310

Purity/Quality:

99% ^*data from raw suppliers

Capsanthin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC(=O)C2(CC(CC2(C)C)O)C)C)C
• Isomeric 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
• Description: Capsanthin is the major colouring compounds contained in the Paprika oleoresin, which is a kind of oil-soluble extract isolated from the fruits Capsicum annuum or Capsicum frutescens, and is a colouring and/or flavouring in food products. As a pink pigment, Capsanthin is very abundant in peppers, accounting for 60% of the proportions of all flavonoids in the peppers. It has antioxidant properties, being able to help the body to scavenge the free radicals as well as inhibiting the growth of cancer cells. Capsanthin is a carotenoid that has been found in C. annuum and has diverse biological activities. It reduces hydrogen peroxide-induced production of reactive oxygen species (ROS) and phosphorylation of ERK and p38 and prevents hydrogen peroxide-induced inhibition of gap junction intercellular communication in WB-F344 rat liver epithelial cells. Capsanthin (0.2 mg/animal) 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 (TPA; ).
• Uses: Capsanthin may be used as an analytical reference standard for the quantification of the analyte in red pepper powder, red pepper fruits, paprika and oleoresin using chromatography techniques. antineoplastic

Technology Process of Capsanthin

There total 20 articles about Capsanthin 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: 42.0%

(all-E)-5-<(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl>-3-methyl-2,4-pentadienyltriphenylphosphonium bromide + (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) → capsanthin (465-42-9)

Guidance literature:

With sodium methylate;

DOI:10.1248/cpb.49.1662

Reference yield:

(R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol (118829-40-6,118829-45-1) → capsanthin (465-42-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Bu₃SnH; AIBN / 0.33 h / 130 °C

1.2: Pd₂dba3*CHCl₃; AsPh₃ / dimethylformamide / 50 °C

2.1: 93 percent / DMAP; Et₃N

3.1: 28 percent / m-CPBA

4.1: LiAlH₄

5.1: MnO₂

6.1: SnCl₄

7.1: HF

8.1: NaOMe

9.1: ion exchange resin Dowex 50W-X₈(H⁺)

10.1: 42 percent / NaOMe

With dmap; manganese(IV) oxide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); ion exchange resin Dowex 50W-X₈(H⁺); hydrogen fluoride; tri-n-butyl-tin hydride; sodium methylate; tin(IV) chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid;

DOI:10.1248/cpb.49.1662

Reference yield:

ethyl (2E,4E)-5-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexyl-1-enyl]-3-methylpenta-2,4-dienoate (395089-68-6) → capsanthin (465-42-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / DMAP; Et₃N

2: 28 percent / m-CPBA

3: LiAlH₄

4: MnO₂

5: SnCl₄

6: HF

7: NaOMe

8: ion exchange resin Dowex 50W-X₈(H⁺)

9: 42 percent / NaOMe

With dmap; manganese(IV) oxide; lithium aluminium tetrahydride; ion exchange resin Dowex 50W-X₈(H⁺); hydrogen fluoride; sodium methylate; tin(IV) chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid;

DOI:10.1248/cpb.49.1662

upstream raw materials:

neocapsanthin B''

neocapsanthin A''

neocapsanthin A'

neocapsanthin B'

Downstream raw materials:

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

capsorubin

neocapsanthin B''

neocapsanthin A''

Refernces

• 1、 Deli, József,Molnár, Péter,Matus, Zoltán,Tóth, Gyula,Steck, Andrea,Pfander, Hanspeter. "Partial Synthesis and Characterization of Capsokarpoxanthins and 3,6-Epoxycapsanthins". . p. 1242 - 1253. Retrieved 2007/10/03.