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465-42-9

Basic Information
CAS No.: 465-42-9
Name: Capsanthin
Article Data: 4
Cas Database
Molecular Structure:
Molecular Structure of 465-42-9 (Capsanthin)
Formula: C40H56O3
Molecular Weight: 584.883
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;
EINECS: 207-364-1
Density: 1.012 g/cm3
Melting Point: 177-178 °C
Boiling Point: 726.6 °C at 760 mmHg
Flash Point: 407.2 °C
Solubility: N/A
Appearance: COA
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
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

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

465-42-9

capsanthin

Conditions
ConditionsYield
With sodium methylate42%

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

465-42-9

capsanthin

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

neocapsanthin B''

A

465-42-9

capsanthin

B

62776-23-2

neocapsanthin A''

C

62741-95-1

neocapsanthin A'

D

62741-96-2

neocapsanthin B'

E

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;
62776-23-2

neocapsanthin A''

A

465-42-9

capsanthin

B

80779-34-6

neocapsanthin B''

C

62741-95-1

neocapsanthin A'

D

62741-96-2

neocapsanthin B'

E

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;
62741-95-1

neocapsanthin A'

A

465-42-9

capsanthin

B

80779-34-6

neocapsanthin B''

C

62776-23-2

neocapsanthin A''

D

62741-96-2

neocapsanthin B'

E

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;
62741-96-2

neocapsanthin B'

A

465-42-9

capsanthin

B

80779-34-6

neocapsanthin B''

C

62776-23-2

neocapsanthin A''

D

62741-95-1

neocapsanthin A'

E

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;
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

465-42-9

capsanthin

B

80779-34-6

neocapsanthin B''

C

62776-23-2

neocapsanthin A''

D

62741-95-1

neocapsanthin A'

E

62741-96-2

neocapsanthin B'

Conditions
ConditionsYield
In pyridine at 74.6 - 95.3℃; Equilibrium constant;
6033-82-5, 25946-06-9

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

A

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

65831-10-9

5,6-Epoxycapsanthin

C

465-42-9

capsanthin

D

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;
118829-40-6, 118829-45-1

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

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
395089-72-2

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

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
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    MSDS/COA Download

    CAPSANTHIN

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  • capsanthin CAS NO. 465-42-9

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Chemistry

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:

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.

Toxicity Data With Reference

1.    

skn-mus TDLo:49.8 µg/kg

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

Safety Profile

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

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.