7542-45-2

Basic information

• Product Name: ASTAXANTHIN
• Synonyms: Astaxanthin (Synthetic) (3 x 30 mg);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
• CAS NO: 7542-45-2
• Molecular Formula: C₄₀H₅₂O₄
• Molecular Weight: 596.84
• EINECS: 231-424-6
• Mol File: 7542-45-2.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 774 °C at 760 mmHg
• Flash Point: 435.8 °C
• Appearance: /
• Density: 1.071
• Storage Temp.: −20°C
• PKA: 12.33±0.70(Predicted)
• CAS DataBase Reference: ASTAXANTHIN(CAS DataBase Reference)
• NIST Chemistry Reference: ASTAXANTHIN(7542-45-2)
• EPA Substance Registry System: ASTAXANTHIN(7542-45-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 7542-45-2(Hazardous Substances Data)

Usage

Description

rac-Astaxanthin is a carotenoid pigment found primarily in marine animals including shrimp and salmon. It is a potent lipid-soluble antioxidant.

Synthetic route

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

Conditions	Yield
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 + tricaprilin (538-23-8) → astaxanthin octanoic acid monoester + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + di-O-octanoyl-all-trans-astaxanthin

Conditions	Yield
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%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + [(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) + semi-astacene (106776-90-3) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
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

tricaprilin (538-23-8) + astaxanthin oleic acid diester → astaxanthin octanoic acid monoester + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + di-O-octanoyl-all-trans-astaxanthin

Conditions	Yield
lipase OF (from Candida) In water at 45℃; for 240h; Product distribution / selectivity; Enzymatic reaction;	A 27.2% B 72.8% C 1%

zeaxanthin (144-68-3) → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2)

Conditions	Yield
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) + astaxanthin oleic acid diester → astaxanthin octanoic acid monoester + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + di-O-octanoyl-all-trans-astaxanthin

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

astaxanthin esters + Octanoic acid (124-07-2) → astaxanthin octanoic acid monoester + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + di-O-octanoyl-all-trans-astaxanthin

Conditions	Yield
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%

astaxanthin esters + tricaprilin (538-23-8) → astaxanthin octanoic acid monoester + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2)

Conditions	Yield
immobilized lipase In hexane; water at 45℃; for 72h; Product distribution / selectivity; Enzymatic reaction;	A 1% B 15.2%

astaxanthin cation radical → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2)

Conditions	Yield
With TX-100 In water Rate constant; Irradiation;

lycopene (502-65-8) + astaxanthin cation radical → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + lycopene radical cation

Conditions	Yield
In benzene Rate constant; pulse radiolysis;

zeaxanthin (144-68-3) + astaxanthin cation radical → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + zeaxanthin radical cation

Conditions	Yield
In benzene Rate constant; pulse radiolysis;

beta-carotene (7235-40-7) + astaxanthin cation radical → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + all-trans β-carotene radical cation

Conditions	Yield
In benzene Rate constant; pulse radiolysis;

astaxanthin dipalmitate (112421-21-3) → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + astaxanthin palmitate (123159-02-4)

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

astaxanthin decanoic acid diester → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + astaxanthin decanoic acid monoester

Conditions	Yield
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 → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + (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	Yield
With water; Candida rugosa lipase at 20℃; for 42h; pH=8.0; Product distribution; Further Variations:; Reagents;

astaxanthin dieicosapentaenoate → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + astaxanthin eicosapentaenoate

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

astaxanthin didocosahexaenoate → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + astaxanthin docosahexaenoate

Conditions	Yield
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) → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2)

Conditions

Yield

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

Conditions

Yield

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

Conditions

Yield

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

Conditions

Yield

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

Conditions	Yield
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) → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2)

Conditions

Yield

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

Conditions

Yield

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

Conditions	Yield
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) → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2)

Conditions

Yield

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

Conditions

Yield

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

Conditions

Yield

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) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → 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)

Conditions	Yield
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) + N-tert-butoxycarbonyl-proline (15761-39-4) → BocProOH ester of astaxanthin

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;	100%

3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + 2,6-bis-tert-butoxycarbonylamino-hexanoic acid (2483-46-7, 65360-27-2, 119962-72-0) → bocLys(boc)OH ester of astaxanthin

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 18h;	100%

dimethyl phosphorobromidate (24167-74-6) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → bis-dimethylphosphate ester of astaxanthin

Conditions	Yield
With methyl imidazole In dichloromethane at 37℃; for 144h;	100%

3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + C16H30N2O6 → C52H76N4O6*4H(1+)

Conditions	Yield
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'-dichlorocanthaxanthin

Conditions	Yield
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) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → astaxanthin dieicosapentaenoate

Conditions	Yield
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) + 1-hexadecylcarboxylic acid (57-10-3) → astaxanthin dipalmitate (112421-21-3)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	92%

docosahexaenoic acid (6217-54-5) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → astaxanthin didocosahexaenoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	91%

Octanoic acid (124-07-2) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → di-O-octanoyl-all-trans-astaxanthin

Conditions	Yield
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) + 4-(dimethylamino)butyric acid hydrochloride (69954-66-1) → (dimethylamino)butyric acid diester of astaxanthin

Conditions	Yield
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 + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + 4-(dimethylamino)butyric acid hydrochloride (69954-66-1) → (dimethylamino)butyric acid diester of astaxanthin + (dimethylamino)butyric acid diester (LVIII)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamide	A 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-formamide	A 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-formamide	A n/a B 77.7%

3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + acetyl chloride (75-36-5) → 3-acetoxy-3'-hydroxycanthaxanthin

Conditions	Yield
With pyridine In dichloromethane at 0℃;	64%

4-morpholinocarbonyl chloride (15159-40-7) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → astaxanthin 4-morpholine monocarbamate + astaxanthin 4-morpholine dicarbamate

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide); dichloromethane at 20℃; for 36h;	A 33.17% B 33.42%

Octanoic acid (124-07-2) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → astaxanthin octanoic acid monoester + di-O-octanoyl-all-trans-astaxanthin

Conditions	Yield
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%

cis-aconitic anhydride (6318-55-4) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → astaxanthin aconitic monoester + astaxanthin aconitic diester

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide); dichloromethane at 20℃; for 36h;	A 13.25% B 27.67%

2-Methoxypropene (116-11-0) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → (3RS,3'RS)-Astaxanthin-bis(1-methoxy-1-methylaethyl)aether

Conditions	Yield
With toluene-4-sulfonic acid at 0℃; for 0.25h;	27%

3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + citric acid (77-92-9) → astaxanthin citric acid monoester + astaxanthin citric acid diester

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane at 20℃; for 36h;	A 26.56% B 7.81%

3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + 4-(dimethylamino)butyric acid hydrochloride (69954-66-1) → dimethylaminobutyric acid monoester of astaxanthin

Conditions	Yield
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) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → astaxanthin octanoic acid monoester + di-O-octanoyl-all-trans-astaxanthin

Conditions	Yield
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%

glutathion (70-18-8) + 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) → glutathione monoester of astaxanthin

Conditions	Yield
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%

Upstream product

• 144-68-3 zeaxanthin 
• 7235-40-7 beta-carotene 
• 144-68-3 zeaxanthin 
• 144-55-8 sodium hydrogencarbonate 
• 1353023-75-2 zeaxanthin t-butyldimethylsilylether 
• 112421-21-3 astaxanthin dipalmitate 
• 5056-17-7 (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial 
• 124-07-2 Octanoic acid 
• 538-23-8 tricaprilin 
• 264279-25-6 ethyl (2E,4E)-3-methyl-5-(2,10,10-trimethyl-4,7-dioxaspiro[4,5]dec-1-en-1-yl)-2,4-pentadienoate 
• 264279-27-8 (2E,4E)-3-methyl-5-(2,10,10-trimethyl-4,7-dioxaspiro[4,5]dec-1-en-1-yl)-2,4-pentadienol 

Downstream Products

• 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 
• 64809-43-4 apo-11-astaxanthinal 
• 80713-42-4 rac-3-Hydroxy-4-oxo-12'-apo-β-carotin-12'-al 

Relevant articles and documents

Method for Improving Flavor of Astaxanthin-Containing Extract

A method for improving the flavor of an astaxanthin-containing extract of the present invention includes the steps of: mixing 0.5 to 1000 parts by weight of ethanol and 1 part by weight of the astaxanthin-containing extract so as to obtain an ethanol mixture; collecting a solid precipitated from the ethanol mixture obtained; and drying the solid collected. In particular, the astaxanthin-containing extract, i.e., the starting material, is an extract from a green alga.

PROCESS FOR THE PREPARATION OF ASTAXANTHIN

The invention therefore relates to a process for the preparation of astaxanthin of the formula I by reacting 2 mol of the triphenylphosphonium salt of the general formula II in which X represents chlorine, bromine or the (HSO4) radical, preferably bromine, in a Wittig reaction with one mol of the C10-dialdehyde of the formula III which is characterized in that a) the starting compounds of the formulae II and III are taken up in a solvent, the mixture is cooled to a temperature of not more than 10°C, preferably -18°C to +5°C, b) about 0.9 to 1.5, preferably 0.9 to 1.2, mol of a base per mole of triphenylphosphonium salt are added to the resulting reaction mixture at a temperature of not more than 10°C, preferably -18°C to +5°C, c) the base is metered and mixed in over a predetermined reaction time T so that at least a ? base equivalent is added to the reaction mixture continuously or quasicontinuously within a timespan T' ?T and the remainder of the base within the remaining reaction time.