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Astaxanthin

Astaxanthin structure

CAS No:
472-61-7
Formula:
C40H52O4
Chemical Name:
Astaxanthin
Synonyms:
β,β-Carotene-4,4′-dione,3,3′-dihydroxy-,(3S,3′S)-;β-Carotene-4,4′-dione,3,3′-dihydroxy-,all-trans-;Astaxanthin;(3S,3′S)-3,3′-Dihydroxy-β,β-carotene-4,4′-dione;Ovoester;Astaxanthin,all-trans-;(3S,3′S)-Astaxanthin;all-trans-Astaxanthin;trans-Astaxanthin;(3S,3′S)-all-trans-Astaxanthin;(3S,3′S)-Astaxanthin;Carophyll Pink;Natupink;BioAstin oleoresin;BioAstin;Lucantin Pink;AstaREAL;NatuRose;AstaXin;Astared;Astots 10O;Astots 5O;Aquasta;(S,S)-Astaxanthin;Astabio AR 5;AstaREAL A1010;Puresta W 05;Astareal ACT;Astacarox;Astabio AR 1;Astax S;Astots ST;all-trans-(3S,3′S)-Astaxanthin;Sunactive AX 310;AstaZine;Astots AWS;Astots 50S;Astabio AP1;346585-67-9
Categories:
Cosmetic Ingredient > Skin Conditioning

Description

Astaxanthin, a red dietary carotenoid isolated from Haematococcus pluvialis, is an inhibitor of PPARγ and a potent antioxidant with antiproliferative, neuroprotective and anti-inflammatory activity[1]. Astaxanthin has potential in the treatment of various diseases, such as cancers and Parkinson’s disease, cardiovascular disease[2]. Due to its bright red colour, Astaxanthin could be used as a food colorant in animal feeds[3].

Astaxanthin Basic Attributes

Molecular Weight：

596.83800

Exact Mass：

596.84

EC Number：

207-451-4

HScode：

3203001990

Characteristics

PSA：

74.60000

XLogP3：

10.3

Appearance：

Solid

Density：

1.071 g/cm3

Melting Point：

182.5 °C

Boiling Point：

774ºC at 760 mmHg

Flash Point：

435.8ºC

Refractive Index：

1.595

Water Solubility：

DMSO: soluble 1mg/mL (warmed);In water, 7.9X10-10 mg/L at 25 deg C (est)

Storage Conditions：

-20ºC

Vapor Pressure：

1.14E-27mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R20/21/22

safety instructions：

S24/25

Marks：

Precautionary statement(s)：

P273, P501

Hazard Statements：

H413

Astaxanthin Use and Manufacturing

Methods of Manufacturing

71, 9 g (0, 125 mol) ASTAXANTHIN-C15-PHOSPHONIUMSALZ P5 (X~ = BRO- mid) wurden in 150 ML Methanol vorgelegt. Bei 0C gab man 11, 4 g GIO-DIAL Ia (95percent ig ; das entspricht 0, 0475 mol) zu. Dann tropfte man innerhalb von 1H bei 0C 24, 8 g einer 30percent igen Lsung von Natriummethylat in Methanol (= 0, 137 mol NaOMe) zu, rhrte eine weitere Stunde bei 0C nach und lies dann auf Raumtemperatur kom- men. Man tropfte eine Lsung von 1, 5 G (25 mmol) Essigsure in 115 ml Wasser zu, erhitzte auf Rckfluss (ca. 75C) und rhrte 20 h unter Rckfluss nach. Man lies auf Raumtemperatur kommen und filtrierte das Kristallisat ab. Der Filterkuchen wurde zweimal MIT JE 100 ML EINES 60 : 40 (V/V) -GEMISCHES AUS METHANOL/WASSER, einmal mit heiem Wasser (100 ml) und einmal mit Methanol (100 ml ; 25C) gewaschen und im Vakuumtrockenschrank bei +50C getrocknet. Auswaage : 23, 5 g Astaxanthin = 83, 0percent Ausbeute (bezogen auf eingesetztes Ia) ; Reinheit nach HPLC : 99, 17percentThe concentrated solution of Example 6 was added dropwise to a solution of triphenylphosphine (11.8 kg) and 1, 2-epoxybutane (130 g) in ethyl acetate (44 kg) at 0 to 30 ° C., and the reaction mixture was added dropwise at the same temperature And the mixture was stirred for 24 hours. The precipitated solid was collected by filtration and the wet crystals were dissolved in methylene chloride (39 kg). The obtained solution was added dropwise to ethyl acetate (305 kg) while stirring, and solid precipitation was confirmed. The precipitated solid was collected by filtration and dried in vacuo to give the title compound (3.95 kg, purity 87.5percent (trans form), 5.8percent (cis form)) as a white solid. The purity of the product was determined by high performance liquid chromatography (column: YMC-PAC ODS-A manufactured by YMC and mobile phase: acetonitrile with 0.1percent trifluoroacetic acid / 0.1percent aqueous trifluoroacetic acid = 5-95 / 45 to 5). 2, 7-dimethylocta-2, 4, 6-triene-1, 8-dialdehyde (0.484 kg), the compound of Example 7 (1) (3.90 kg), 2, 6-di-t-butyl-p-cresol (32.5 g) and 1, 2-epoxybutane (1.9 kg) were suspended in 2-propanol (15 kg) and the suspension was heated under reflux for 30 hours under a nitrogen atmosphere. The reaction mixture was cooled to -5 to 5 ° C. and stirred for 1 hour, and the precipitated solid was collected by filtration to give the title compound (1.53 kg, yield 86.9percent, purity 98.8percent, optical purity 97. 9percent ee) as a deep violet solid. The purity of the product was determined by high performance liquid chromatography (column: Triart C 18 ExRS Plus manufactured by YMC and mobile phase: acetonitrile with 0.025percent trifluoroacetic acid / 0.025percent aqueous trifluoroacetic acid = 30 to 98 / 2), respectively. The optical purity of the product was determined using high performance liquid chromatography (column: YMC CHIRAL Cellulose-SB manufactured by YMC and mobile phase: hexane / tetrahydrofuran = 85/15)

Uses

Carotenoid pigment found mostly in animal organisms, but also occuring in plants; thought to be the precursor of astacin. Animal studies indicate that it reduces blood glucose and ameliorates several parameters of the diabetic metabolic syndrome. It improves blood flow and vascular tone in models of hypertension.

Related Drugs

Astaxanthin Soft Capsules
Specifications	0.6g/tablet

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