465-42-9

Basic information

• Product Name: Capsanthin
• Synonyms: Capsanthin;3,3'-Dihydroxy-beta,kappa-caroten-6'one;Capsanthin/capsorubin;Paprika extract;beta,kappa-Caroten-6'one, 3,3'dihydroxy-;(3R,3'S,5'R)-3,3'-Dihydroxy-beta,kappa-caroten-6'-one
• CAS NO: 465-42-9
• Molecular Formula: C₄₀H₅₆O₃
• Molecular Weight: 584.8708
• EINECS: 207-364-1
• Product Categories: Thiophenes ,Thiazolines/Thiazolidines;Carotenoids
• Mol File: 465-42-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 177-178℃
• Boiling Point: 726.6 °C at 760 mmHg
• Flash Point: 407.2 °C
• Appearance: COA
• Density: 1.012 g/cm³
• Vapor Pressure: 2.22E-24mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 14.85±0.60(Predicted)
• Stability: Light Sensitive, Temperature Sensitive
• Merck: 14,1769
• CAS DataBase Reference: Capsanthin(CAS DataBase Reference)
• NIST Chemistry Reference: Capsanthin(465-42-9)
• EPA Substance Registry System: Capsanthin(465-42-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 465-42-9(Hazardous Substances Data)

Usage

Uses

Used in Food Industry:
Capsanthin is used as a colorant and/or flavoring agent in food products due to its vibrant red color and natural origin.
Used in Analytical Chemistry:
Capsanthin serves as an analytical reference standard for the quantification of the analyte in red pepper powder, red pepper fruits, paprika, and oleoresin using chromatography techniques.
Used in Antineoplastic Applications:
Capsanthin is used as an anti-cancer agent, reducing the number of colonic aberrant crypt foci and preneoplastic lesions in a rat model of N-methylnitrosourea-induced colon carcinogenesis. It also exhibits anti-inflammatory properties by reducing ear edema in a mouse model of inflammation induced by phorbol 12-myristate 13-acetate (TPA). Additionally, it has been found to reduce hydrogen peroxide-induced production of reactive oxygen species (ROS) and phosphorylation of ERK and p38, as well as preventing hydrogen peroxide-induced inhibition of gap junction intercellular communication in WB-F344 rat liver epithelial cells.

References

http://www.botanical-online.com/english/capsanthin_properites.htm https://en.wikipedia.org/wiki/Paprika_oleoresin

Biochem/physiol Actions

Capsanthin is a potential nutraceutical, is found in green vegetables and is a constituent of paprika and asparagus. Capsanthin has been shown to exhibit anti-proliferative function.

Safety Profile

A poison by skin contact. When heated to decomposition it emits acrid smoke and irritating vapors.

Purification Methods

Possible impurities are zeaxanthin and capsorubin (below). Purify capsanthin by chromatography on a column of alumina (grade IV) and develop with 0.2% EtOH in *C6H6. It

InChI:InChI=1/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

Synthetic route

(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)

Conditions	Yield
With sodium methylate	42%

(all-E,3R,5'R)-3-hydroxy-β,κ-carotene-3',6'-dione → capsanthin (465-42-9)

Conditions	Yield
(i) LiAlH4, THF, (ii) chloranil, benzene; Multistep reaction;

neocapsanthin B'' (80779-34-6) → capsanthin (465-42-9) + neocapsanthin A'' (62776-23-2) + neocapsanthin A' (62741-95-1) + neocapsanthin B' (62741-96-2) + (2E,4E,6E,8E,10Z,12E,14E,16E,18E)-19-((R)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-((1R,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl)-4,8,13,17-tetramethyl-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one (147383-92-4)

Conditions	Yield
In pyridine at 74.6 - 95.3℃; Equilibrium constant;

neocapsanthin A'' (62776-23-2) → capsanthin (465-42-9) + neocapsanthin B'' (80779-34-6) + neocapsanthin A' (62741-95-1) + neocapsanthin B' (62741-96-2) + (2E,4E,6E,8E,10Z,12E,14E,16E,18E)-19-((R)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-((1R,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl)-4,8,13,17-tetramethyl-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one (147383-92-4)

Conditions	Yield
In pyridine at 74.6 - 95.3℃; Equilibrium constant;

neocapsanthin A' (62741-95-1) → capsanthin (465-42-9) + neocapsanthin B'' (80779-34-6) + neocapsanthin A'' (62776-23-2) + neocapsanthin B' (62741-96-2) + (2E,4E,6E,8E,10Z,12E,14E,16E,18E)-19-((R)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-((1R,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl)-4,8,13,17-tetramethyl-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one (147383-92-4)

Conditions	Yield
In pyridine at 74.6 - 95.3℃; Equilibrium constant;

neocapsanthin B' (62741-96-2) → capsanthin (465-42-9) + neocapsanthin B'' (80779-34-6) + neocapsanthin A'' (62776-23-2) + neocapsanthin A' (62741-95-1) + (2E,4E,6E,8E,10Z,12E,14E,16E,18E)-19-((R)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-((1R,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl)-4,8,13,17-tetramethyl-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one (147383-92-4)

Conditions	Yield
In pyridine at 74.6 - 95.3℃; Equilibrium constant;

(2E,4E,6E,8E,10Z,12E,14E,16E,18E)-19-((R)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-((1R,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl)-4,8,13,17-tetramethyl-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one (147383-92-4) → capsanthin (465-42-9) + neocapsanthin B'' (80779-34-6) + neocapsanthin A'' (62776-23-2) + neocapsanthin A' (62741-95-1) + neocapsanthin B' (62741-96-2)

Conditions	Yield
In pyridine at 74.6 - 95.3℃; Equilibrium constant;

(3R,3'S,5'R)-3,3'-diacetoxy-β,κ-caroten-6'-one (6033-82-5, 25946-06-9) → (3S,5Ξ,8Ξ,3'S,5'R)-5,8-epoxy-3,3'-dihydroxy-5,8-dihydro-β,κ-caroten-6'-one (65790-19-4, 65831-12-1, 65831-13-2, 65831-14-3, 104012-89-7) + 5,6-Epoxycapsanthin (65831-10-9) + capsanthin (465-42-9) + all-trans-capsanthin 5,6-epoxide (65831-11-0)

Conditions	Yield
With potassium hydroxide; monoperoxyphthalic acid 1.) Et2O, r.t., 75 h; 2.) MeOH, Et2O, 16 h; Yield given. Multistep reaction;

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

Conditions	Yield
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 View Scheme
Multi-step reaction with 11 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: 64 percent / PdCl2(MeCN)2; Et3N 11.1: 42 percent / NaOMe View Scheme
Multi-step reaction with 11 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: 70 percent / PdCl2(MeCN)2; Et3N 11.1: 42 percent / NaOMe View Scheme
Multi-step reaction with 4 steps 1.1: Bu3SnH; AIBN / 0.33 h / 130 °C 1.2: Pd2dba3*CHCl3; AsPh3 / dimethylformamide / 50 °C 2.1: LiAlH4 3.1: 42 percent / NaOMe View Scheme

(2E,4E)-6-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-3-methyl-6-oxohexa-2,4-dienal (395089-72-2) → capsanthin (465-42-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOMe 2: ion exchange resin Dowex 50W-X8(H+) 3: 42 percent / NaOMe View Scheme
Multi-step reaction with 4 steps 1: NaOMe 2: ion exchange resin Dowex 50W-X8(H+) 3: 64 percent / PdCl2(MeCN)2; Et3N 4: 42 percent / NaOMe View Scheme
Multi-step reaction with 4 steps 1: NaOMe 2: ion exchange resin Dowex 50W-X8(H+) 3: 70 percent / PdCl2(MeCN)2; Et3N 4: 42 percent / NaOMe View Scheme

(R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol (956982-07-3) → capsanthin (465-42-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 42 percent / NaOMe View Scheme

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)

Conditions	Yield
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 View Scheme
Multi-step reaction with 10 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: 64 percent / PdCl2(MeCN)2; Et3N 10: 42 percent / NaOMe View Scheme
Multi-step reaction with 10 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: 70 percent / PdCl2(MeCN)2; Et3N 10: 42 percent / NaOMe View Scheme
Multi-step reaction with 3 steps 1: LiAlH4 2: 42 percent / NaOMe View Scheme

(2E,4E)-6-[(1R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-3-methyl-6-oxo-hexa-2,4-dienal (1027513-29-6) → capsanthin (465-42-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: HF 2: NaOMe 3: ion exchange resin Dowex 50W-X8(H+) 4: 42 percent / NaOMe View Scheme
Multi-step reaction with 5 steps 1: HF 2: NaOMe 3: ion exchange resin Dowex 50W-X8(H+) 4: 64 percent / PdCl2(MeCN)2; Et3N 5: 42 percent / NaOMe View Scheme
Multi-step reaction with 5 steps 1: HF 2: NaOMe 3: ion exchange resin Dowex 50W-X8(H+) 4: 70 percent / PdCl2(MeCN)2; Et3N 5: 42 percent / NaOMe View Scheme

(2E,4E)-3-methyl-5-[(1S,4S,6R)-4-tert-butyldimethylsilyloxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]penta-2,4-dienal (395089-71-1) → capsanthin (465-42-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: SnCl4 2: HF 3: NaOMe 4: ion exchange resin Dowex 50W-X8(H+) 5: 42 percent / NaOMe View Scheme
Multi-step reaction with 6 steps 1: SnCl4 2: HF 3: NaOMe 4: ion exchange resin Dowex 50W-X8(H+) 5: 64 percent / PdCl2(MeCN)2; Et3N 6: 42 percent / NaOMe View Scheme
Multi-step reaction with 6 steps 1: SnCl4 2: HF 3: NaOMe 4: ion exchange resin Dowex 50W-X8(H+) 5: 70 percent / PdCl2(MeCN)2; Et3N 6: 42 percent / NaOMe View Scheme

(2E,4E)-5-[(1S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl]-3-methyl-penta-2,4-dien-1-ol → capsanthin (465-42-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: MnO2 2: SnCl4 3: HF 4: NaOMe 5: ion exchange resin Dowex 50W-X8(H+) 6: 42 percent / NaOMe View Scheme
Multi-step reaction with 7 steps 1: MnO2 2: SnCl4 3: HF 4: NaOMe 5: ion exchange resin Dowex 50W-X8(H+) 6: 64 percent / PdCl2(MeCN)2; Et3N 7: 42 percent / NaOMe View Scheme
Multi-step reaction with 7 steps 1: MnO2 2: SnCl4 3: HF 4: NaOMe 5: ion exchange resin Dowex 50W-X8(H+) 6: 70 percent / PdCl2(MeCN)2; Et3N 7: 42 percent / NaOMe View Scheme

ethyl (2E,4E)-5-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohexyl-1-enyl]-3-methylpenta-2,4-dienoate (395089-69-7) → capsanthin (465-42-9)

Conditions	Yield
Multi-step reaction with 8 steps 1: 28 percent / m-CPBA 2: LiAlH4 3: MnO2 4: SnCl4 5: HF 6: NaOMe 7: ion exchange resin Dowex 50W-X8(H+) 8: 42 percent / NaOMe View Scheme
Multi-step reaction with 9 steps 1: 28 percent / m-CPBA 2: LiAlH4 3: MnO2 4: SnCl4 5: HF 6: NaOMe 7: ion exchange resin Dowex 50W-X8(H+) 8: 64 percent / PdCl2(MeCN)2; Et3N 9: 42 percent / NaOMe View Scheme
Multi-step reaction with 9 steps 1: 28 percent / m-CPBA 2: LiAlH4 3: MnO2 4: SnCl4 5: HF 6: NaOMe 7: ion exchange resin Dowex 50W-X8(H+) 8: 70 percent / PdCl2(MeCN)2; Et3N 9: 42 percent / NaOMe View Scheme

(2E,4E,6E,8E,10E,12E)-1-((1R,4S)-4-Hydroxy-1,2,2-trimethyl-cyclopentyl)-14,14-dimethoxy-4,8,13-trimethyl-tetradeca-2,4,6,8,10,12-hexaen-1-one → capsanthin (465-42-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: ion exchange resin Dowex 50W-X8(H+) 2: 42 percent / NaOMe View Scheme
Multi-step reaction with 3 steps 1: ion exchange resin Dowex 50W-X8(H+) 2: 64 percent / PdCl2(MeCN)2; Et3N 3: 42 percent / NaOMe View Scheme
Multi-step reaction with 3 steps 1: ion exchange resin Dowex 50W-X8(H+) 2: 70 percent / PdCl2(MeCN)2; Et3N 3: 42 percent / NaOMe View Scheme

(2E,4E)-5-[(1S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl]-3-methyl-penta-2,4-dienoic acid ethyl ester (395089-70-0) → capsanthin (465-42-9)

Conditions	Yield
Multi-step reaction with 7 steps 1: LiAlH4 2: MnO2 3: SnCl4 4: HF 5: NaOMe 6: ion exchange resin Dowex 50W-X8(H+) 7: 42 percent / NaOMe View Scheme
Multi-step reaction with 8 steps 1: LiAlH4 2: MnO2 3: SnCl4 4: HF 5: NaOMe 6: ion exchange resin Dowex 50W-X8(H+) 7: 64 percent / PdCl2(MeCN)2; Et3N 8: 42 percent / NaOMe View Scheme
Multi-step reaction with 8 steps 1: LiAlH4 2: MnO2 3: SnCl4 4: HF 5: NaOMe 6: ion exchange resin Dowex 50W-X8(H+) 7: 70 percent / PdCl2(MeCN)2; Et3N 8: 42 percent / NaOMe View Scheme

(2E,4E,6Z,8Z,10E,12E)-14-((1R,4S)-4-Hydroxy-1,2,2-trimethyl-cyclopentyl)-2,7,11-trimethyl-14-oxo-tetradeca-2,4,6,8,10,12-hexaenal → capsanthin (465-42-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / PdCl2(MeCN)2; Et3N 2: 42 percent / NaOMe View Scheme

(2E,4Z,6Z,8E,10E,12E)-14-((1R,4S)-4-Hydroxy-1,2,2-trimethyl-cyclopentyl)-2,7,11-trimethyl-14-oxo-tetradeca-2,4,6,8,10,12-hexaenal → capsanthin (465-42-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / PdCl2(MeCN)2; Et3N 2: 42 percent / NaOMe View Scheme

capsanthin (465-42-9) + acetyl chloride (75-36-5) → (3R,3'S,5'R)-3,3'-diacetoxy-β,κ-caroten-6'-one (6033-82-5, 25946-06-9)

Conditions	Yield
With pyridine

capsanthin (465-42-9) → (2E,4E,6E,8E,10E,12E,14E,16E,18E)-4,8,13,17-Tetramethyl-19-(2,6,6-trimethyl-cyclohexa-1,4-dienyl)-1-((R)-1,2,2-trimethyl-cyclopent-3-enyl)-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-ol

Conditions	Yield
(i) LiAlH4, (ii) HCl, CHCl3; Multistep reaction;

capsanthin (465-42-9) → (all-E,3R,5'R)-3-hydroxy-β,κ-carotene-3',6'-dione

Conditions	Yield
With aluminum tri-tert-butoxide In acetone; benzene

diazomethane (186581-53-3, 908094-01-9) + capsanthin (465-42-9) → (1R,4S)-4-Hydroxy-1,2,2-trimethycyclopentancarbonsaeure-methylester (65243-74-5)

Conditions	Yield
With dihydrogen peroxide; oxygen; ozone 1.) carbon tetrachloride, acetic acid, water, reflux, 2 h, 2.) ether, 0 deg C; Yield given. Multistep reaction;

capsanthin (465-42-9) → neocapsanthin B'' (80779-34-6) + neocapsanthin A'' (62776-23-2) + neocapsanthin A' (62741-95-1) + neocapsanthin B' (62741-96-2)

Conditions	Yield
iodine Irradiation;

capsanthin (465-42-9) → neocapsanthin B'' (80779-34-6) + neocapsanthin A'' (62776-23-2) + neocapsanthin A' (62741-95-1) + neocapsanthin B' (62741-96-2) + (2E,4E,6E,8E,10Z,12E,14E,16E,18E)-19-((R)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-((1R,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl)-4,8,13,17-tetramethyl-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one (147383-92-4)

Conditions	Yield
In pyridine at 74.6 - 95.3℃; Kinetics; Equilibrium constant; Thermodynamic data; EA, ΔH, ΔS, ΔG;

capsanthin (465-42-9) + aq.-ethanolic KOH → β-citraurin

Conditions	Yield
at 80℃;

capsanthin (465-42-9) + iodine (7553-56-2) + benzene (71-43-2) → ((3R,3'S,5'R)-3,3'-dihydroxy-13-cis-β,κ-caroten-6'-one) + ((3R,3'S,5'R)-3,3'-dihydroxy-13'-cis-β,κ-caroten-6'-one) + ((3R,3'S,5'R)-3,3'-dihydroxy-9-cis-β,κ-caroten-6'-one) + ((3R,3'S,5'R)-3,3'-dihydroxy-9'-cis-β,κ-caroten-6'-one)

capsanthin (465-42-9) → neocapsanthin-A + neocapsanthin-B + neocapsanthin-C

Conditions	Yield
at 180℃;

capsanthin (465-42-9) + benzene (71-43-2) → neocapsanthin-A + neocapsanthin-B + neocapsanthin-C

capsanthin (465-42-9) + iodine (7553-56-2) + benzene (71-43-2) → neocapsanthin-A + neocapsanthin-B + neocapsanthin-C

Upstream product

• 147383-92-4 (2E,4E,6E,8E,10Z,12E,14E,16E,18E)-19-((R)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-((1R,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl)-4,8,13,17-tetramethyl-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one 
• 395089-70-0 (2E,4E)-5-[(1S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl]-3-methyl-penta-2,4-dienoic acid ethyl ester 
• 395089-69-7 ethyl (2E,4E)-5-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohexyl-1-enyl]-3-methylpenta-2,4-dienoate 
• 395089-71-1 (2E,4E)-3-methyl-5-[(1S,4S,6R)-4-tert-butyldimethylsilyloxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]penta-2,4-dienal 
• 1027513-29-6 (2E,4E)-6-[(1R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-3-methyl-6-oxo-hexa-2,4-dienal 
• 395089-68-6 ethyl (2E,4E)-5-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexyl-1-enyl]-3-methylpenta-2,4-dienoate 
• 956982-07-3 (R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol 
• 395089-72-2 (2E,4E)-6-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-3-methyl-6-oxohexa-2,4-dienal 
• 118829-40-6 (R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol 
• 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 
• 6033-82-5 (3R,3'S,5'R)-3,3'-diacetoxy-β,κ-caroten-6'-one 
• 62741-96-2 neocapsanthin B' 
• 62741-95-1 neocapsanthin A' 
• 62776-23-2 neocapsanthin A'' 

Downstream Products

• 80779-34-6 neocapsanthin B'' 
• 62776-23-2 neocapsanthin A'' 
• 62741-95-1 neocapsanthin A' 
• 62741-96-2 neocapsanthin B' 
• 147383-92-4 (2E,4E,6E,8E,10Z,12E,14E,16E,18E)-19-((R)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-((1R,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl)-4,8,13,17-tetramethyl-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one 
• 65243-75-6 <(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon 
• 470-38-2 capsorubin 
• 6033-82-5 (3R,3'S,5'R)-3,3'-diacetoxy-β,κ-caroten-6'-one 

Relevant articles and documents

Total synthesis of capsanthin using Lewis acid-promoted regio- and stereoselective rearrangement of tetrasubstituted epoxide

The synthesis of capsanthin 1 was accomplished via the C15-cyclopentyl ketone 13 prepared by Lewis acid-promoted regio-and stereoselective rearrangement of the epoxide 12.

Partial Synthesis and Characterization of Capsokarpoxanthins and 3,6-Epoxycapsanthins

The acid-catalyzed hydrolysis of (3S,5R,6S,3′S,5′R)-5,6-epoxycapsanthin (5) led to (3S,5R,6R,3′S,5′R)- (7) and (3S,5R,6S,3′S,5′R)-capsokarpoxanthin (8). In addition, (3S,5R,8R,3′S,5′R)- (9), (3S,5R,8S,3′S,5′R)-capsochrome (10), and (3S,5R,6R,3′S,5′R)-3,6-epoxycapsanthin (11) were obtained. The acid-catalyzed hydrolysis of (35,55,6R,3′S,5′R)-5,6-epoxycapsanthin (6) afforded (3S,5S,6R,3′S,5′R)-capsokarpoxanthin (12), (3S,5S,8S,3′S,5′R)- (13) and (3S,5S,8R,3′S,5′S)-capsochrome (14) as well as (3S,5S,6R,3′S,5′R)-3,6-epoxyepicapsanthin (15). Compounds 5-15 were isolated in crystalline form and characterized by their UV/VIS, CD, 1H- and 13C-NMR, and mass spectra.

Kinetic Studies on the Thermal (Z/E)-Isomerization of C40-Carotenoids

Rates of thermal (Z/E)-isomerization among all-E-, 9(9')Z-, 13Z-, 13'Z- and 15Z-isomers of zeaxanthin (1), natural violaxanthin (2), "semi-synthetic" violaxanthin (2a), capsorubin (3), capsanthin (4) and lutein epoxide (5) have been measured at temperatures over the range 333.4-368.4 K.From the specific rate constants calculated on the basis of four kinetic models, the Arrhenius and activation parameters have been derived.The effect of the different end groups and different solvents on the composition of the (Z/E)-equilibrium mixtures have been investigated as well.The rates of the isomerization reactions have been measured by HPLC, UV/VIS spectrophotometry and "classic" column chromatography.