Product Name

  • Name

    ASTAXANTHIN

  • EINECS 231-424-6
  • CAS No. 7542-45-2
  • Article Data23
  • CAS DataBase
  • Density 1.071 g/cm3
  • Solubility
  • Melting Point
  • Formula C40H52O4
  • Boiling Point 774 °C at 760 mmHg
  • Molecular Weight 596.85
  • Flash Point 435.8 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 7542-45-2 (ASTAXANTHIN)
  • Hazard Symbols
  • Synonyms OVEOSTER;AXN;3,3-DIHYDROXY-B,B-CAROTENE-4,4-DIONE;3,3-DIHYDROXY-B,B-CAROTENE-4,4-DIONE;3,3-dihydro-beta,beta-carotene-4,4-dione;.beta.,.beta.-Carotene-4,4-dione, 3,3-dihydroxy-;Einecs 231-424-6;3,3-Dihydroxy-beta-carotene-4,4-dione
  • PSA 74.60000
  • LogP 8.90540

Synthetic route

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial
5056-17-7

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

[(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide

[(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Stage #1: (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial; [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide With ethyloxirane In isopropyl alcohol for 18h; Heating / reflux;
Stage #2: In dichloromethane Heating / reflux;		80%
In various solvent(s) at 63℃; for 20h; Condensation; Wittig reaction;55%
With ethyloxirane at 63℃; for 20h;54.7%
astaxanthin esters

astaxanthin esters

tricaprilin
538-23-8

tricaprilin

A

astaxanthin octanoic acid monoester

astaxanthin octanoic acid monoester

B

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

C

di-O-octanoyl-all-trans-astaxanthin

di-O-octanoyl-all-trans-astaxanthin

Conditions
ConditionsYield
lipase PL (from Alcaligenes) In water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;A 4%
B 79.3%
C 1%
immobilized lipase In water at 45℃; for 96h; Product distribution / selectivity; Enzymatic reaction;A 12.2%
B 64%
C 1%
immobilized lipase of Phenyl Toyopearl In water at 45℃; for 96h; Product distribution / selectivity; Enzymatic reaction;A 14.1%
B 61.6%
C 2.8%
...Expand
(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial
5056-17-7

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

[(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide

[(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide

A

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

B

semi-astacene
106776-90-3

semi-astacene

C

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
Stage #1: (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial; [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide With sodium methylate In methanol; dichloromethane at -5℃; for 19.6 - 20.5h;
Stage #2: With acetic acid In methanol; dichloromethane Product distribution / selectivity;		A 75.8%
B n/a
C n/a
...Expand
tricaprilin
538-23-8

tricaprilin

astaxanthin oleic acid diester

astaxanthin oleic acid diester

A

astaxanthin octanoic acid monoester

astaxanthin octanoic acid monoester

B

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

C

di-O-octanoyl-all-trans-astaxanthin

di-O-octanoyl-all-trans-astaxanthin

Conditions
ConditionsYield
lipase OF (from Candida) In water at 45℃; for 240h; Product distribution / selectivity; Enzymatic reaction;A 27.2%
B 72.8%
C 1%
...Expand
zeaxanthin
144-68-3

zeaxanthin

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
With sodium bromate; sodium hydrogensulfite In chloroform at 20 - 30℃; for 3h;72.14%
With sodium bromate; sodium hydrogensulfite In chloroform for 0.5h;51%
Octanoic acid
124-07-2

Octanoic acid

astaxanthin oleic acid diester

astaxanthin oleic acid diester

A

astaxanthin octanoic acid monoester

astaxanthin octanoic acid monoester

B

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

C

di-O-octanoyl-all-trans-astaxanthin

di-O-octanoyl-all-trans-astaxanthin

Conditions
ConditionsYield
lipase OF (from Candida) In water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;A 8.2%
B 61.1%
C 1%
...Expand
astaxanthin esters

astaxanthin esters

Octanoic acid
124-07-2

Octanoic acid

A

astaxanthin octanoic acid monoester

astaxanthin octanoic acid monoester

B

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

C

di-O-octanoyl-all-trans-astaxanthin

di-O-octanoyl-all-trans-astaxanthin

Conditions
ConditionsYield
lipase OF (from Candida) In water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;A 10.5%
B 42.6%
C 1%
immobilized lipase In water at 45℃; for 96h; Product distribution / selectivity; Enzymatic reaction;A 2%
B 23.6%
C 1%
...Expand
astaxanthin esters

astaxanthin esters

tricaprilin
538-23-8

tricaprilin

A

astaxanthin octanoic acid monoester

astaxanthin octanoic acid monoester

B

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
immobilized lipase In hexane; water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;A 1%
B 15.2%
...Expand
astaxanthin cation radical

astaxanthin cation radical

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
With TX-100 In water Rate constant; Irradiation;
lycopene
502-65-8

lycopene

astaxanthin cation radical

astaxanthin cation radical

A

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

B

lycopene radical cation

lycopene radical cation

Conditions
ConditionsYield
In benzene Rate constant; pulse radiolysis;
...Expand
zeaxanthin
144-68-3

zeaxanthin

astaxanthin cation radical

astaxanthin cation radical

A

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

B

zeaxanthin radical cation

zeaxanthin radical cation

Conditions
ConditionsYield
In benzene Rate constant; pulse radiolysis;
...Expand
beta-carotene
7235-40-7

beta-carotene

astaxanthin cation radical

astaxanthin cation radical

A

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

B

all-trans β-carotene radical cation

all-trans β-carotene radical cation

Conditions
ConditionsYield
In benzene Rate constant; pulse radiolysis;
...Expand
astaxanthin dipalmitate
112421-21-3

astaxanthin dipalmitate

A

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

B

astaxanthin palmitate
123159-02-4

astaxanthin palmitate

Conditions
ConditionsYield
With rainbow trout intestine lipolytic enzymes; water at 20℃; for 48h; pH=8.0; Product distribution; Further Variations:; Reagents;
astaxanthin decanoic acid diester

astaxanthin decanoic acid diester

A

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

B

astaxanthin decanoic acid monoester

astaxanthin decanoic acid monoester

Conditions
ConditionsYield
With water; Candida rugosa lipase at 20℃; for 42h; pH=8.0; Product distribution; Further Variations:; Reagents;
(E)-Octadec-9-enoic acid 3,5,5-trimethyl-2-oxo-4-{(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-[2,6,6-trimethyl-4-((E)-octadec-9-enoyloxy)-3-oxo-cyclohex-1-enyl]-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl}-cyclohex-3-enyl ester

(E)-Octadec-9-enoic acid 3,5,5-trimethyl-2-oxo-4-{(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-[2,6,6-trimethyl-4-((E)-octadec-9-enoyloxy)-3-oxo-cyclohex-1-enyl]-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl}-cyclohex-3-enyl ester

A

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

B

(E)-Octadec-9-enoic acid 4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl)-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl ester

(E)-Octadec-9-enoic acid 4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl)-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl ester

Conditions
ConditionsYield
With water; Candida rugosa lipase at 20℃; for 42h; pH=8.0; Product distribution; Further Variations:; Reagents;
astaxanthin dieicosapentaenoate

astaxanthin dieicosapentaenoate

A

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

B

astaxanthin eicosapentaenoate

astaxanthin eicosapentaenoate

Conditions
ConditionsYield
With rainbow trout intestine lipolytic enzymes; water at 20℃; for 48h; pH=8.0; Product distribution; Further Variations:; Reagents;
astaxanthin didocosahexaenoate

astaxanthin didocosahexaenoate

A

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

B

astaxanthin docosahexaenoate

astaxanthin docosahexaenoate

Conditions
ConditionsYield
With rainbow trout intestine lipolytic enzymes; water at 20℃; for 48h; pH=8.0; Product distribution; Further Variations:; Reagents;
6-Methyl-hept-5-en-2-on
110-93-0

6-Methyl-hept-5-en-2-on

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: NaH / tetrahydrofuran / 0 - 20 °C
1.2: 89.4 percent / tetrahydrofuran / 2 h / 20 °C
2.1: 86 percent / conc. H2SO4 / nitromethane / 0.5 h / 0 °C
3.1: 95 percent / m-chloroperbenzoic acid / ethyl acetate / 0 - 20 °C
4.1: 96.5 percent / LDA / tetrahydrofuran / -40 - 20 °C
5.1: 66 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C
6.1: p-toluenesulfonic acid; trimethyl orthoformate
6.2: 89 percent / HCl / acetone
7.1: 72 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C
8.1: nBuLi / tetrahydrofuran / -20 °C
8.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C
9.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C
10.1: 97 percent / HCl / acetone; H2O
11.1: LDA / tetrahydrofuran / 0.17 h / -20 °C
11.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C
12.1: HBr / CH2Cl2 / 0 °C
13.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C
14.1: 55 percent / various solvent(s) / 20 h / 63 °C
View Scheme
geranonitrile
5146-66-7

geranonitrile

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 86 percent / conc. H2SO4 / nitromethane / 0.5 h / 0 °C
2.1: 95 percent / m-chloroperbenzoic acid / ethyl acetate / 0 - 20 °C
3.1: 96.5 percent / LDA / tetrahydrofuran / -40 - 20 °C
4.1: 66 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C
5.1: p-toluenesulfonic acid; trimethyl orthoformate
5.2: 89 percent / HCl / acetone
6.1: 72 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C
7.1: nBuLi / tetrahydrofuran / -20 °C
7.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C
8.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C
9.1: 97 percent / HCl / acetone; H2O
10.1: LDA / tetrahydrofuran / 0.17 h / -20 °C
10.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C
11.1: HBr / CH2Cl2 / 0 °C
12.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C
13.1: 55 percent / various solvent(s) / 20 h / 63 °C
View Scheme
5-methyl-4-hexenenitrile
23089-87-4

5-methyl-4-hexenenitrile

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: 70 percent / diethyl ether / 1 h / 0 °C
2.1: NaH / tetrahydrofuran / 0 - 20 °C
2.2: 89.4 percent / tetrahydrofuran / 2 h / 20 °C
3.1: 86 percent / conc. H2SO4 / nitromethane / 0.5 h / 0 °C
4.1: 95 percent / m-chloroperbenzoic acid / ethyl acetate / 0 - 20 °C
5.1: 96.5 percent / LDA / tetrahydrofuran / -40 - 20 °C
6.1: 66 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C
7.1: p-toluenesulfonic acid; trimethyl orthoformate
7.2: 89 percent / HCl / acetone
8.1: 72 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C
9.1: nBuLi / tetrahydrofuran / -20 °C
9.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C
10.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C
11.1: 97 percent / HCl / acetone; H2O
12.1: LDA / tetrahydrofuran / 0.17 h / -20 °C
12.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C
13.1: HBr / CH2Cl2 / 0 °C
14.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C
15.1: 55 percent / various solvent(s) / 20 h / 63 °C
View Scheme
2,6,6-trimethyl-2-cyclohexenecarbonitrile
57524-13-7

2,6,6-trimethyl-2-cyclohexenecarbonitrile

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 95 percent / m-chloroperbenzoic acid / ethyl acetate / 0 - 20 °C
2.1: 96.5 percent / LDA / tetrahydrofuran / -40 - 20 °C
3.1: 66 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C
4.1: p-toluenesulfonic acid; trimethyl orthoformate
4.2: 89 percent / HCl / acetone
5.1: 72 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C
6.1: nBuLi / tetrahydrofuran / -20 °C
6.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C
7.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C
8.1: 97 percent / HCl / acetone; H2O
9.1: LDA / tetrahydrofuran / 0.17 h / -20 °C
9.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C
10.1: HBr / CH2Cl2 / 0 °C
11.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C
12.1: 55 percent / various solvent(s) / 20 h / 63 °C
View Scheme
(2E,4E)-3-methyl-5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4-pentadienol
29538-78-1

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4-pentadienol

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: LDA / tetrahydrofuran / 0.17 h / -20 °C
1.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C
2.1: HBr / CH2Cl2 / 0 °C
3.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C
4.1: 55 percent / various solvent(s) / 20 h / 63 °C
View Scheme
2,4,4-Trimethylcyclohex-2-en-1-one-3-carbonitrile
56830-39-8

2,4,4-Trimethylcyclohex-2-en-1-one-3-carbonitrile

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: p-toluenesulfonic acid; trimethyl orthoformate
1.2: 89 percent / HCl / acetone
2.1: 72 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C
3.1: nBuLi / tetrahydrofuran / -20 °C
3.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C
4.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C
5.1: 97 percent / HCl / acetone; H2O
6.1: LDA / tetrahydrofuran / 0.17 h / -20 °C
6.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C
7.1: HBr / CH2Cl2 / 0 °C
8.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C
9.1: 55 percent / various solvent(s) / 20 h / 63 °C
View Scheme
3-hydroxy-2,6,6-trimethyl-2-cyclohexenecarbonitrile
145106-79-2

3-hydroxy-2,6,6-trimethyl-2-cyclohexenecarbonitrile

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 66 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C
2.1: p-toluenesulfonic acid; trimethyl orthoformate
2.2: 89 percent / HCl / acetone
3.1: 72 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C
4.1: nBuLi / tetrahydrofuran / -20 °C
4.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C
5.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C
6.1: 97 percent / HCl / acetone; H2O
7.1: LDA / tetrahydrofuran / 0.17 h / -20 °C
7.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C
8.1: HBr / CH2Cl2 / 0 °C
9.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C
10.1: 55 percent / various solvent(s) / 20 h / 63 °C
View Scheme
(2E,4E)-3-methyl-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4-pentadienol
94669-81-5

(2E,4E)-3-methyl-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4-pentadienol

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HBr / CH2Cl2 / 0 °C
2: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C
3: 55 percent / various solvent(s) / 20 h / 63 °C
View Scheme
2,3-epoxy-2,6,6-trimethyl-1-cyclohexanecarbonitrile
264279-20-1

2,3-epoxy-2,6,6-trimethyl-1-cyclohexanecarbonitrile

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 96.5 percent / LDA / tetrahydrofuran / -40 - 20 °C
2.1: 66 percent / pyridinium chlorochromate / CH2Cl2 / 0 - 20 °C
3.1: p-toluenesulfonic acid; trimethyl orthoformate
3.2: 89 percent / HCl / acetone
4.1: 72 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C
5.1: nBuLi / tetrahydrofuran / -20 °C
5.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C
6.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C
7.1: 97 percent / HCl / acetone; H2O
8.1: LDA / tetrahydrofuran / 0.17 h / -20 °C
8.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C
9.1: HBr / CH2Cl2 / 0 °C
10.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C
11.1: 55 percent / various solvent(s) / 20 h / 63 °C
View Scheme
2,10,10-trimethyl-4,7-dioxaspiro[4,5]dec-1-enecarbaldehyde
264279-23-4

2,10,10-trimethyl-4,7-dioxaspiro[4,5]dec-1-enecarbaldehyde

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: nBuLi / tetrahydrofuran / -20 °C
1.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C
2.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C
3.1: 97 percent / HCl / acetone; H2O
4.1: LDA / tetrahydrofuran / 0.17 h / -20 °C
4.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C
5.1: HBr / CH2Cl2 / 0 °C
6.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C
7.1: 55 percent / various solvent(s) / 20 h / 63 °C
View Scheme
2,10,10-trimethyl-4,7-oxadispiro[4,5]dec-1-enecarbonitrile
264279-22-3

2,10,10-trimethyl-4,7-oxadispiro[4,5]dec-1-enecarbonitrile

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 72 percent / DIBAL-H / petroleum ether / 1 h / -60 - 20 °C
2.1: nBuLi / tetrahydrofuran / -20 °C
2.2: 79 percent / tetrahydrofuran / 1 h / 0 - 20 °C
3.1: 52 percent / DIBAL-H / petroleum ether / -80 - -20 °C
4.1: 97 percent / HCl / acetone; H2O
5.1: LDA / tetrahydrofuran / 0.17 h / -20 °C
5.2: 69 percent / (+)-(8,8-dichlorocamphorsulfonyl)oxaziridine / tetrahydrofuran / 1.25 h / -20 - 20 °C
6.1: HBr / CH2Cl2 / 0 °C
7.1: 1,2-epoxybutane / ethyl acetate / 24 h / 20 °C
8.1: 55 percent / various solvent(s) / 20 h / 63 °C
View Scheme
succinic acid anhydride
108-30-5

succinic acid anhydride

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

rac-succinic acid mono-(4-{18-[4-(3-carboxy-propionyloxy)-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl}-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl) ester
769935-71-9

rac-succinic acid mono-(4-{18-[4-(3-carboxy-propionyloxy)-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl}-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl) ester

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 48h;100%
With dmap In dichloromethane at 20℃; for 14h; Inert atmosphere; Darkness;
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 48h;
3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

N-tert-butoxycarbonyl-proline
15761-39-4

N-tert-butoxycarbonyl-proline

BocProOH ester of astaxanthin

BocProOH ester of astaxanthin

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;100%
3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

2,6-bis-tert-butoxycarbonylamino-hexanoic acid
2483-46-7, 65360-27-2, 119962-72-0

2,6-bis-tert-butoxycarbonylamino-hexanoic acid

bocLys(boc)OH ester of astaxanthin

bocLys(boc)OH ester of astaxanthin

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 18h;100%
dimethyl phosphorobromidate
24167-74-6

dimethyl phosphorobromidate

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

bis-dimethylphosphate ester of astaxanthin

bis-dimethylphosphate ester of astaxanthin

Conditions
ConditionsYield
With methyl imidazole In dichloromethane at 37℃; for 144h;100%
3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

C16H30N2O6

C16H30N2O6

C52H76N4O6*4H(1+)

C52H76N4O6*4H(1+)

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane for 18h; Darkness; Inert atmosphere;100%
3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

3,3'-dichlorocanthaxanthin

3,3'-dichlorocanthaxanthin

Conditions
ConditionsYield
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 20℃;95%
Multi-step reaction with 2 steps
1: pyridine / CH2Cl2 / 0 °C
2: n-Bu4NCl / tetrahydrofuran
View Scheme
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

all cis-5,8,11,14,17-eicosapentaenoic acid

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

astaxanthin dieicosapentaenoate

astaxanthin dieicosapentaenoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;92%
3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

astaxanthin dipalmitate
112421-21-3

astaxanthin dipalmitate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;92%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

astaxanthin didocosahexaenoate

astaxanthin didocosahexaenoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;91%
Octanoic acid
124-07-2

Octanoic acid

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

di-O-octanoyl-all-trans-astaxanthin

di-O-octanoyl-all-trans-astaxanthin

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 19h;90%
3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

4-(dimethylamino)butyric acid hydrochloride
69954-66-1

4-(dimethylamino)butyric acid hydrochloride

(dimethylamino)butyric acid diester of astaxanthin

(dimethylamino)butyric acid diester of astaxanthin

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In DMF (N,N-dimethyl-formamide); dichloromethane at 20℃; for 36h;77.7%
HOBT-H2O

HOBT-H2O

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

4-(dimethylamino)butyric acid hydrochloride
69954-66-1

4-(dimethylamino)butyric acid hydrochloride

A

(dimethylamino)butyric acid diester of astaxanthin

(dimethylamino)butyric acid diester of astaxanthin

B

(dimethylamino)butyric acid diester (LVIII)

(dimethylamino)butyric acid diester (LVIII)

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamideA n/a
B 77.7%
With dmap; N-ethyl-N,N-diisopropylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamideA n/a
B 77.7%
With dmap; N-ethyl-N,N-diisopropylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamideA n/a
B 77.7%
...Expand
3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

acetyl chloride
75-36-5

acetyl chloride

3-acetoxy-3'-hydroxycanthaxanthin

3-acetoxy-3'-hydroxycanthaxanthin

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃;64%
4-morpholinocarbonyl chloride
15159-40-7

4-morpholinocarbonyl chloride

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

A

astaxanthin 4-morpholine monocarbamate

astaxanthin 4-morpholine monocarbamate

B

astaxanthin 4-morpholine dicarbamate

astaxanthin 4-morpholine dicarbamate

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide); dichloromethane at 20℃; for 36h;A 33.17%
B 33.42%
...Expand
Octanoic acid
124-07-2

Octanoic acid

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

A

astaxanthin octanoic acid monoester

astaxanthin octanoic acid monoester

B

di-O-octanoyl-all-trans-astaxanthin

di-O-octanoyl-all-trans-astaxanthin

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;A 32%
B 22%
lipase OF (from Candida) In water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;A 6%
B 1%
immobilized lipase In water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;A 4.2%
B 1%
...Expand
cis-aconitic anhydride
6318-55-4

cis-aconitic anhydride

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

A

astaxanthin aconitic monoester

astaxanthin aconitic monoester

B

astaxanthin aconitic diester

astaxanthin aconitic diester

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide); dichloromethane at 20℃; for 36h;A 13.25%
B 27.67%
...Expand
2-Methoxypropene
116-11-0

2-Methoxypropene

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

(3RS,3'RS)-Astaxanthin-bis(1-methoxy-1-methylaethyl)aether

(3RS,3'RS)-Astaxanthin-bis(1-methoxy-1-methylaethyl)aether

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 0℃; for 0.25h;27%
3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

citric acid
77-92-9

citric acid

A

astaxanthin citric acid monoester

astaxanthin citric acid monoester

B

astaxanthin citric acid diester

astaxanthin citric acid diester

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane at 20℃; for 36h;A 26.56%
B 7.81%
...Expand
3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

4-(dimethylamino)butyric acid hydrochloride
69954-66-1

4-(dimethylamino)butyric acid hydrochloride

dimethylaminobutyric acid monoester of astaxanthin

dimethylaminobutyric acid monoester of astaxanthin

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide); dichloromethane at 20℃; for 36h;24.5%
With dmap; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 36h;24.5%
tricaprilin
538-23-8

tricaprilin

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

A

astaxanthin octanoic acid monoester

astaxanthin octanoic acid monoester

B

di-O-octanoyl-all-trans-astaxanthin

di-O-octanoyl-all-trans-astaxanthin

Conditions
ConditionsYield
immobilized lipase In hexane; water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;A 23.9%
B 2.3%
immobilized lipase In water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;A 21.9%
B 2.6%
HPA25 resin-immobilized lipase In water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;A 19.2%
B 1%
...Expand
glutathion
70-18-8

glutathion

3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

glutathione monoester of astaxanthin

glutathione monoester of astaxanthin

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In DMF (N,N-dimethyl-formamide); dichloromethane at 20℃; for 36h;23.61%

3,3'-Dihydro-beta,beta-carotene-4,4'-dione Specification

The 3,3'-Dihydroxy-β,β-carotene-4,4'-dione with CAS registry number of 7542-45-2 is also called Astaxanthin. Its IUPAC name is 6-Hydroxy-3-[(1E,3E,5E,7Z,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethylcyclohex-2-en-1-one,and systematic name is called 3,3'-Dihydroxy-β,β-carotene-4,4'-dione. Its EINECS registry number is 231-424-6.

Physical properties about 3,3'-Dihydro-beta,beta-carotene-4,4'-dione are: (1)ACD/LogP:  9.526; (2)# of Rule of 5 Violations:  2  ; (3)ACD/LogD (pH 5.5):  9.53; (4)ACD/LogD (pH 7.4):  9.53; (5)ACD/BCF (pH 5.5):  1000000.00; (6)ACD/BCF (pH 7.4):  1000000.00; (7)ACD/KOC (pH 5.5):  3625797.00; (8)ACD/KOC (pH 7.4):  3625797.00; (9)#H bond acceptors:  2; (10)#H bond donors:  0; (11)#Freely Rotating Bonds:  10; (12)Index of Refraction:  1.575; (13)Molar Refractivity:  186.196 cm3; (14)Molar Volume:  563.125 cm3; (15)Surface Tension:  39.3440017700195 dyne/cm; (16)Density:  1.003 g/cm3; (17)Flash Point:  253.949 °C; (18)Enthalpy of Vaporization:  104.774 kJ/mol; (19)Boiling Point:  716.954 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C2\C(=C(\C=C\C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(\C(=O)CCC1(C)C)C)C)C)C)C)C(C)(C)CC2)C;
(2)Std. InChI:InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-23-35-33(5)37(41)25-27-39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-36-34(6)38(42)26-28-40(36,9)10/h11-24H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+;
(3)Std. InChIKey:FDSDTBUPSURDBL-DKLMTRRASA-N.

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