Encyclopedia / Pharmaceutical / Cardiovascular Agents / Herbal Extract

Astaxanthin

CAS：472-61-7
MW:596.83848
MF：C40H52O4

Natural astaxanthin also known as astacin, is a kind of precious health ingredients, is used for development to enhance immunity, anti-oxidation, anti-inflammatory, eyes and brain health, regulating blood lipids and other natural and healthy products. At present, the main used as a raw material for human health food and medicine; aquaculture (currently the main salmon, trout and salmon), poultry feed additive and additives of cosmetics. It can significantly improve the body's immunity, because of its non-specific combination with skeletal muscle, can effectively remove the free radicals which are generated by the movement of the muscle cells, strengthen aerobic metabolism, so it has a significant anti fatigue effect. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Astaxanthin

1.2 Synonyms: (3S,3’S)-3,3’-Dihydroxy-.beta.,.beta.-carotene-4,4’-dione; (3S,3'S)-3,3'-Dihydroxy-Β,Β-carotene-4,4'-dione; (3S,3'S)-all-trans-Astaxanthin; (3S,3'S)-Astaxanthin; 3,3'-DIHYDROXY-B,B-CAROTENE-4,4'-DIONE; 3,3-DIHYDROXY-B,B-CAROTENE-4,4-DIONE; 3,3'-DIHYDROXY-BETA,BETA-CAROTENE-4,4'-DIONE; 3,3'-Dihydroxy-Β,Β-carotene-4,4'-dione; all-trans-Astaxanthin; AstaREAL; Astaxanthin Discontinued; Astaxanthin(3,3-Dihydroxy-Beta,Beta-Carotene-4,4-Dione); AXN; BioAstin; BioAstin oleoresin; Carophyll Pink; EINECS 207-451-4; HAEMATOCOCCUS PLUVIALIS; Lucantin Pink; MFCD00672621; Natupink; Β,Β-Carotene-4,4'-dione, 3,3'-dihydroxy-, (3S,3'S)-;

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1.3 CAS No.: 472-61-7

1.4 CID: 5281224

1.5 EINECS: 207-451-4

1.6 Molecular Formula: C40H52O4

1.7 Inchi: InChI=1S/C40H52O4/c1-27(17-13-19-29(3)21-23-33-31(5)37(43)35(41)25-39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)38(44)36(42)26-40(34,9)10/h11-24,35-36,41-42H,25-26H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,27-15+,28-16+,29-19+,30-20+/t35-,36-/m0/s1

1.8 InChkey: MQZIGYBFDRPAKN-UWFIBFSHSA-N

1.9 Canonical Smiles: CC1=C(C(CC(C1=O)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(C(=O)C(CC2(C)C)O)C)C)C

1.10 Isomers Smiles: CC1=C(C(C[C@@H](C1=O)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C(=O)[C@H](CC2(C)C)O)C)\C)\C)/C)/C

2. Properties

2.1 Solubility: DMSO: soluble1mg/mL (warmed)

2.2 Appearance: Solid

2.3 Chemical Properties: Drak-Purple Solid

2.4 Color/Form: Red powder

2.5 pKa: 12.33±0.70(Predicted)

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

2.7 Spectral Properties: UV max: 503 nm (CS2); 472 nm (methanol); 466-467 nm (hexane); 485 nm (chloroform)

2.8 StorageTemp: ?20°C

3. Use and Manufacturing

3.1 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].

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3.2 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)

View all

3.3 Usage: Natural astaxanthin also known as astacin, is a kind of precious health ingredients, is used for development to enhance immunity, anti-oxidation, anti-inflammatory, eyes and brain health, regulating blood lipids and other natural and healthy products. At present, the main used as a raw material for human health food and medicine; aquaculture (currently the main salmon, trout and salmon), poultry feed additive and additives of cosmetics. It can significantly improve the body's immunity, because of its non-specific combination with skeletal muscle, can effectively remove the free radicals which are generated by the movement of the muscle cells, strengthen aerobic metabolism, so it has a significant anti fatigue effect.

View all

4. Safety and Handling

4.1 Exposure Standards and Regulations: Certification of this color additive when used as a food is not necessary for the protection of the public health, and therefore batches thereof are exempt from the certification pursuant to section 721(c) of the act.

4.2 Octanol/Water Partition Coefficient: log Kow = 13.27 (est)

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

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4.4 Safety: Hazard Codes:?Xn
Risk Statements: 20/21/22-36/37/38?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26?
S24/25:Avoid contact with skin and eyes.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
WGK Germany?of Astaxanthin (CAS NO.472-61-7):??3

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4.5 Specification: ? Astaxanthin (CAS NO.472-61-7), its Synonyms are 3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione, (3S,3'S)- ; Astaxanthin, (3S,3'S)- ; Astaxanthin, all-trans-, (3S,3'S)- ; beta,beta-Carotene-4,4'-dione, 3,3'-dihydroxy-, (3S,3'S)- ; (3S,3'S)-3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione ; 3,3'-Dihydroxy-beta-carotene-4,4'-dione ; Astaxanthine .

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

Predict 1H proton NMR

7. Synthesis Route

472-61-7Total: 3 Synthesis Route

6094-35-5

472-61-7 367 Suppliers

7542-45-2 32 Suppliers

472-61-7 367 Suppliers

60760-95-4

71772-51-5 1 Suppliers

8. Precursor and Product

precursor:

6094-35-5

7542-45-2

72523-68-3

9. Computed Properties

Molecular Weight：596.83848g/mol
Molecular Formula：C₄₀H₅₂O₄
Compound Is Canonicalized：True
Exact Mass：10.3
XLogP3-AA：596.38656014
Monoisotopic Mass：596.38656014
Complexity：1340
Rotatable Bond Count：10
Hydrogen Bond Donor Count：2
Hydrogen Bond Acceptor Count：4
Topological Polar Surface Area：74.6
Heavy Atom Count：：44
Defined Atom Stereocenter Count：2
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：9
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADcfB8OAAAAAAAAAAAAAAAAAAAAAAAAAAgQAAAAAAAAAAAAAAAGgAACAAADhSggAICAAAAAgCIAqBSAAIAAAAgAAAICAFAAEgIEBIAAQAAQAAEwAAIgQOIiMAPAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

Storage Conditions: 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)

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11. Toltal 329 Suppliers View more

CANGZHOU ENKE PHARMA-TECH CO.,LTD

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Tel: Update Time:2024/11/12

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Astaxanthin 472-61-7 Good quality Natural AXN powder extracted from haematococcus pluvialis

Hubei Jiutian Bio-medical Technology Co., Ltd

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Tel: Update Time:2024/09/17

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Hot sale Superior Quality Factory stock Astaxanthin CAS 472-61-7 For Wholesale

Tianjin Furun Tongda International Trade Co., LTD

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Tel: Update Time:2024/11/15

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Hebei Crovell Biotech Co. Ltd

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Baoji Guokang Healthchem co.,ltd

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Tel: Update Time:2024/11/15

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12. Related Questions

: What are the Health Benefits of Astaxanthin, the Powerful Antioxidant?Astaxanthin: The Powerful Antioxidant Astaxanthin is a valuable red pigment and antioxidant extensively utilized in pharmaceuticals, cosmetics, and the food industry. Belonging to the carotenoid group..; What is Astaxanthin and How is it Produced?What is Astaxanthin? Astaxanthin, a keto-carotenoid, is a lipid-soluble pigment that belongs to the terpenes class of chemical compounds. It is classified as a xanthophyll and is known for its red-ora..; How does Astaxanthin exist?Astaxanthin can be produced by certain algae, bacteria, and fungi. Some aquatic species, such as crustaceans including shrimp, consume these algae and plankton, and then store Astaxanthin in their she..; Who is Astaxanthin suitable for?Young people face significant work and study pressures, often requiring business trips or working overtime, which can lead to decreased eyesight and disrupted metabolism. To restore physical fitness, ..

13. Realated Product Infomation