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465-42-9 Usage

Description

Capsanthin is a carotenoid compound found in Paprika oleoresin, an oil-soluble extract derived from the fruits of Capsicum annuum or Capsicum frutescens. It is a pink pigment that constitutes 60% of all flavonoids in peppers and exhibits antioxidant properties, helping to scavenge free radicals and inhibit the growth of cancer cells.

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

Check Digit Verification of cas no

The CAS Registry Mumber 465-42-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,6 and 5 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 465-42:
(5*4)+(4*6)+(3*5)+(2*4)+(1*2)=69
69 % 10 = 9
So 465-42-9 is a valid CAS Registry Number.
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

465-42-9 Well-known Company Product Price

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  • TCI America

  • (C0781)  Capsanthin (=Paprika Extract) (Vegetable oil solution)  

  • 465-42-9

  • 25g

  • 735.00CNY

  • Detail
  • Sigma-Aldrich

  • (94863)  Capsanthin  analytical standard

  • 465-42-9

  • 94863-1MG

  • 9,395.10CNY

  • Detail

465-42-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name capsanthin

1.2 Other means of identification

Product number -
Other names Capsanthin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food Additives: COLOUR
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:465-42-9 SDS

465-42-9Synthetic 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

465-42-9Relevant articles and documents

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

Yamano,Ito

, p. 1662 - 1663 (2007/10/03)

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.

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

Molnar, Peter,Kortvelyesi, Tarnas,Matus, Zoltan,Szabolca, Jozsef

, p. 801 - 841 (2007/10/03)

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.

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