Name: Capsanthin
SKU: 465-42-9

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Basic Information

Molecular Structure:
CAS No.:	465-42-9
Name:	Capsanthin
Article Data:	4

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
Appearance:	COA
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

Conditions	Yield
With sodium methylate	42%

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

: 465-42-9
capsanthin

Conditions

Conditions	Yield
(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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

: 118829-40-6, 118829-45-1
(R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol

: 465-42-9
capsanthin

Conditions

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

: 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

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

Total:123 Page 1 of 4 1 2 3 4 Next>>

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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

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.

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Chemistry

Uses

Toxicity Data With Reference

Safety Profile

Specification