Product Name

  • Name

    Capsanthin

  • EINECS 207-364-1
  • CAS No. 465-42-9
  • Article Data4
  • CAS DataBase
  • Density 1.012 g/cm3
  • Solubility
  • Melting Point 177-178 °C
  • Formula C40H56O3
  • Boiling Point 726.6 °C at 760 mmHg
  • Molecular Weight 584.883
  • Flash Point 407.2 °C
  • Transport Information
  • Appearance COA
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 465-42-9 (Capsanthin)
  • Hazard Symbols
  • 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;
  • PSA 57.53000
  • LogP 9.80630

Synthetic route

(all-E)-5-<(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl>-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

(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

(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

capsanthin
465-42-9

capsanthin

Conditions
ConditionsYield
With sodium methylate42%
(all-E,3R,5'R)-3-hydroxy-β,κ-carotene-3',6'-dione

(all-E,3R,5'R)-3-hydroxy-β,κ-carotene-3',6'-dione

capsanthin
465-42-9

capsanthin

Conditions
ConditionsYield
(i) LiAlH4, THF, (ii) chloranil, benzene; Multistep reaction;
neocapsanthin B''
80779-34-6

neocapsanthin B''

A

capsanthin
465-42-9

capsanthin

B

neocapsanthin A''
62776-23-2

neocapsanthin A''

C

neocapsanthin A'
62741-95-1

neocapsanthin A'

D

neocapsanthin B'
62741-96-2

neocapsanthin B'

E

(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

(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

Conditions
ConditionsYield
In pyridine at 74.6 - 95.3℃; Equilibrium constant;
neocapsanthin A''
62776-23-2

neocapsanthin A''

A

capsanthin
465-42-9

capsanthin

B

neocapsanthin B''
80779-34-6

neocapsanthin B''

C

neocapsanthin A'
62741-95-1

neocapsanthin A'

D

neocapsanthin B'
62741-96-2

neocapsanthin B'

E

(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

(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

Conditions
ConditionsYield
In pyridine at 74.6 - 95.3℃; Equilibrium constant;
neocapsanthin A'
62741-95-1

neocapsanthin A'

A

capsanthin
465-42-9

capsanthin

B

neocapsanthin B''
80779-34-6

neocapsanthin B''

C

neocapsanthin A''
62776-23-2

neocapsanthin A''

D

neocapsanthin B'
62741-96-2

neocapsanthin B'

E

(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

(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

Conditions
ConditionsYield
In pyridine at 74.6 - 95.3℃; Equilibrium constant;
neocapsanthin B'
62741-96-2

neocapsanthin B'

A

capsanthin
465-42-9

capsanthin

B

neocapsanthin B''
80779-34-6

neocapsanthin B''

C

neocapsanthin A''
62776-23-2

neocapsanthin A''

D

neocapsanthin A'
62741-95-1

neocapsanthin A'

E

(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

(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

Conditions
ConditionsYield
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

(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

A

capsanthin
465-42-9

capsanthin

B

neocapsanthin B''
80779-34-6

neocapsanthin B''

C

neocapsanthin A''
62776-23-2

neocapsanthin A''

D

neocapsanthin A'
62741-95-1

neocapsanthin A'

E

neocapsanthin B'
62741-96-2

neocapsanthin B'

Conditions
ConditionsYield
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

(3R,3'S,5'R)-3,3'-diacetoxy-β,κ-caroten-6'-one

A

(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

(3S,5Ξ,8Ξ,3'S,5'R)-5,8-epoxy-3,3'-dihydroxy-5,8-dihydro-β,κ-caroten-6'-one

B

5,6-Epoxycapsanthin
65831-10-9

5,6-Epoxycapsanthin

C

capsanthin
465-42-9

capsanthin

D

all-trans-capsanthin 5,6-epoxide
65831-11-0

all-trans-capsanthin 5,6-epoxide

Conditions
ConditionsYield
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

(R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol

capsanthin
465-42-9

capsanthin

Conditions
ConditionsYield
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

(2E,4E)-6-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-3-methyl-6-oxohexa-2,4-dienal

capsanthin
465-42-9

capsanthin

Conditions
ConditionsYield
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

(R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol

capsanthin
465-42-9

capsanthin

Conditions
ConditionsYield
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

ethyl (2E,4E)-5-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexyl-1-enyl]-3-methylpenta-2,4-dienoate

capsanthin
465-42-9

capsanthin

Conditions
ConditionsYield
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

(2E,4E)-6-[(1R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1,2,2-trimethyl-cyclopentyl]-3-methyl-6-oxo-hexa-2,4-dienal

capsanthin
465-42-9

capsanthin

Conditions
ConditionsYield
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

(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

capsanthin
465-42-9

capsanthin

Conditions
ConditionsYield
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

(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

capsanthin

Conditions
ConditionsYield
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

ethyl (2E,4E)-5-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohexyl-1-enyl]-3-methylpenta-2,4-dienoate

capsanthin
465-42-9

capsanthin

Conditions
ConditionsYield
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

(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

capsanthin

Conditions
ConditionsYield
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

(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

capsanthin
465-42-9

capsanthin

Conditions
ConditionsYield
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

(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

capsanthin

Conditions
ConditionsYield
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

(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

capsanthin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / PdCl2(MeCN)2; Et3N
2: 42 percent / NaOMe
View Scheme
capsanthin
465-42-9

capsanthin

acetyl chloride
75-36-5

acetyl chloride

(3R,3'S,5'R)-3,3'-diacetoxy-β,κ-caroten-6'-one
6033-82-5, 25946-06-9

(3R,3'S,5'R)-3,3'-diacetoxy-β,κ-caroten-6'-one

Conditions
ConditionsYield
With pyridine
capsanthin
465-42-9

capsanthin

(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

(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
ConditionsYield
(i) LiAlH4, (ii) HCl, CHCl3; Multistep reaction;
capsanthin
465-42-9

capsanthin

(all-E,3R,5'R)-3-hydroxy-β,κ-carotene-3',6'-dione

(all-E,3R,5'R)-3-hydroxy-β,κ-carotene-3',6'-dione

Conditions
ConditionsYield
With aluminum tri-tert-butoxide In acetone; benzene
capsanthin
465-42-9

capsanthin

(1R,4S)-4-Hydroxy-1,2,2-trimethycyclopentancarbonsaeure-methylester
65243-74-5

(1R,4S)-4-Hydroxy-1,2,2-trimethycyclopentancarbonsaeure-methylester

Conditions
ConditionsYield
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

capsanthin

A

neocapsanthin B''
80779-34-6

neocapsanthin B''

B

neocapsanthin A''
62776-23-2

neocapsanthin A''

C

neocapsanthin A'
62741-95-1

neocapsanthin A'

D

neocapsanthin B'
62741-96-2

neocapsanthin B'

Conditions
ConditionsYield
iodine Irradiation;
capsanthin
465-42-9

capsanthin

A

neocapsanthin B''
80779-34-6

neocapsanthin B''

B

neocapsanthin A''
62776-23-2

neocapsanthin A''

C

neocapsanthin A'
62741-95-1

neocapsanthin A'

D

neocapsanthin B'
62741-96-2

neocapsanthin B'

E

(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

(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

Conditions
ConditionsYield
In pyridine at 74.6 - 95.3℃; Kinetics; Equilibrium constant; Thermodynamic data; EA, ΔH, ΔS, ΔG;
capsanthin
465-42-9

capsanthin

aq.-ethanolic KOH

aq.-ethanolic KOH

β-citraurin

β-citraurin

Conditions
ConditionsYield
at 80℃;
capsanthin
465-42-9

capsanthin

iodine
7553-56-2

iodine

benzene
71-43-2

benzene

A

((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)

B

((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)

C

((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)

D

((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

capsanthin

A

neocapsanthin-A

neocapsanthin-A

B

neocapsanthin-B

neocapsanthin-B

C

neocapsanthin-C

neocapsanthin-C

Conditions
ConditionsYield
at 180℃;
capsanthin
465-42-9

capsanthin

benzene
71-43-2

benzene

A

neocapsanthin-A

neocapsanthin-A

B

neocapsanthin-B

neocapsanthin-B

C

neocapsanthin-C

neocapsanthin-C

capsanthin
465-42-9

capsanthin

iodine
7553-56-2

iodine

benzene
71-43-2

benzene

A

neocapsanthin-A

neocapsanthin-A

B

neocapsanthin-B

neocapsanthin-B

C

neocapsanthin-C

neocapsanthin-C

Capsanthin Chemical Properties

Chemistry informtion about Capsanthin (CAS NO.465-42-9) is:
IUPAC Name:  (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
Synonyms: 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 
Molecular Weight: 584.87084 [g/mol]
Molecular Formula: C40H56O3
XLogP3-AA: 10.6
H-Bond Donor: 2
H-Bond Acceptor: 3
EINECS: 207-364-1 
Density: 1.012 g/cm3
Flash Point: 407.2 °C
Boiling Point: 726.6 °C at 760 mmHg
Vapour Pressure: 2.22E-24 mmHg at 25°C 
Enthalpy of Vaporization: 121.17 kJ/mol
Following is the molecular structure of Capsanthin (CAS NO.465-42-9) is:

Capsanthin Uses

As Paprika excerpt Capsanthin (CAS NO.465-42-9) was used in oil and water-soluble commercial preparations to the colouring of meat and Fischkonserven, sweet goods (Marzipan), Mayonnaisen, sausages as well as of Kosmetika. Also as feed additive for Eidotter and skin pigmentation of mast poultry the two coloring materials use find.

Capsanthin Toxicity Data With Reference

1.    

skn-mus TDLo:49.8 µg/kg

    CALEDQ    Cancer Letters (Shannon, Ireland). 172 (2001),103.

Capsanthin Safety Profile

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

Capsanthin Specification

 Capsanthin (CAS NO.465-42-9) is the head Carotinoid of the Paprikafrucht (Capsicum annuum, Solanaceae). From their Capsanthin as well as Capsorubin and a row are isolated from Apocarotinoiden.

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