(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
Conditions | Yield |
---|---|
With sodium methylate | 42% |
capsanthin
Conditions | Yield |
---|---|
(i) LiAlH4, THF, (ii) chloranil, benzene; Multistep reaction; |
neocapsanthin B''
A
capsanthin
B
neocapsanthin A''
C
neocapsanthin A'
D
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
Conditions | Yield |
---|---|
In pyridine at 74.6 - 95.3℃; Equilibrium constant; |
neocapsanthin A''
A
capsanthin
B
neocapsanthin B''
C
neocapsanthin A'
D
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
Conditions | Yield |
---|---|
In pyridine at 74.6 - 95.3℃; Equilibrium constant; |
neocapsanthin A'
A
capsanthin
B
neocapsanthin B''
C
neocapsanthin A''
D
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
Conditions | Yield |
---|---|
In pyridine at 74.6 - 95.3℃; Equilibrium constant; |
neocapsanthin B'
A
capsanthin
B
neocapsanthin B''
C
neocapsanthin A''
D
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
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
A
capsanthin
B
neocapsanthin B''
C
neocapsanthin A''
D
neocapsanthin A'
E
neocapsanthin B'
Conditions | Yield |
---|---|
In pyridine at 74.6 - 95.3℃; Equilibrium constant; |
(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
B
5,6-Epoxycapsanthin
C
capsanthin
D
all-trans-capsanthin 5,6-epoxide
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
capsanthin
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
capsanthin
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
capsanthin
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
capsanthin
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
capsanthin
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
capsanthin
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 |
capsanthin
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
capsanthin
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 |
capsanthin
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
capsanthin
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 |
capsanthin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 64 percent / PdCl2(MeCN)2; Et3N 2: 42 percent / NaOMe View Scheme |
capsanthin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / PdCl2(MeCN)2; Et3N 2: 42 percent / NaOMe View Scheme |
capsanthin
acetyl chloride
(3R,3'S,5'R)-3,3'-diacetoxy-β,κ-caroten-6'-one
Conditions | Yield |
---|---|
With pyridine |
capsanthin
Conditions | Yield |
---|---|
(i) LiAlH4, (ii) HCl, CHCl3; Multistep reaction; |
capsanthin
Conditions | Yield |
---|---|
With aluminum tri-tert-butoxide In acetone; benzene |
diazomethane
capsanthin
(1R,4S)-4-Hydroxy-1,2,2-trimethycyclopentancarbonsaeure-methylester
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
A
neocapsanthin B''
B
neocapsanthin A''
C
neocapsanthin A'
D
neocapsanthin B'
Conditions | Yield |
---|---|
iodine Irradiation; |
capsanthin
A
neocapsanthin B''
B
neocapsanthin A''
C
neocapsanthin A'
D
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
Conditions | Yield |
---|---|
In pyridine at 74.6 - 95.3℃; Kinetics; Equilibrium constant; Thermodynamic data; EA, ΔH, ΔS, ΔG; |
Conditions | Yield |
---|---|
at 80℃; |
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:
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.
1. | skn-mus TDLo:49.8 µg/kg | CALEDQ Cancer Letters (Shannon, Ireland). 172 (2001),103. |
A poison by skin contact. When heated to decomposition it emits acrid smoke and irritating vapors.
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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