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Factory Supply Astaxanthin
Cas No: 472-61-7
No Data 1 Gram 1000 Kilogram/Day Ality Chemical Corporation Contact Supplier
Astaxanthin
Cas No: 472-61-7
USD $ 150.0-1000.0 / Kilogram 1 Kilogram 5000 Metric Ton/Day Kono Chem Co.,Ltd Contact Supplier
Astaxanthin
Cas No: 472-61-7
No Data 1 Kilogram 1 Metric Ton/Month Hangzhou Think Chemical Co. Ltd Contact Supplier
Astaxanthin Powder
Cas No: 472-61-7
USD $ 30.0-30.0 / Kilogram 1 Kilogram 300 Kilogram/Month Greenutra Resource Inc Contact Supplier
Pure Haematococcus Pluvialis Extract Powder Astaxanthin 10% Feed Grade Astaxanthin
Cas No: 472-61-7
USD $ 105.0-257.0 / Kilogram 1 Kilogram 100000000 Kilogram/Year Xi'an Quanao Biotech Co., Ltd. Contact Supplier
Natural Haematococcus pluvialis extract Astaxanthin Powder
Cas No: 472-61-7
USD $ 370.0-370.0 / Kilogram 1 Kilogram 1000 Kilogram/Week Xi'an Harmonious Natural Bio-Technology Co., Ltd. Contact Supplier
CAS No. 472-61-7 Astaxanthin
Cas No: 472-61-7
No Data 1 Kilogram 100 Metric Ton/Month Guangdong Juda Chemical Industrial Co.,Limited Contact Supplier
Haematococcus Pluvialis Extract Astaxanthin Powder
Cas No: 472-61-7
USD $ 188.0-188.0 / Kilogram 1 Kilogram 2000 Kilogram/Day ShangHai Soyoung Biotechnology Inc Contact Supplier
High quality Astaxanthin powder
Cas No: 472-61-7
USD $ 100.0-200.0 / Kilogram 1 Kilogram 1000 Kilogram/Month Binbo Biological Co., Ltd Contact Supplier
Astaxanthin Manufacturer/High quality/Best price/In stock
Cas No: 472-61-7
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier

472-61-7 Usage

Product features

Shrimp flavin is found in river crayfish shell, oysters and salmon, which is a sort of red carotenoid, It can be combined with the protein in vivo and show green, blue. There are antioxidant, anti-aging, anti-tumor, prevention of cardiovascular and cerebrovascular disease. Astaxanthin is a kind of lutein, the most widely distributed in the animal kingdom. It is pink, and has unique coloring function, also can promote antibody production, enhancing animal immunity. On the aspects of the antioxidant and scavenging free radicals, the ability is stronger than β-carotene( (10 times). It is soluble in water and lipophilic, soluble in carbon disulfide, acetone, benzene and chloroform and other organic solvents. Astaxanthin is a kind of very potential carotenoid additives, and has a broad prospect in food, feed, cosmetics, pharmaceuticals and other fields. Foods which are rich in the astaxanthin include marine plants, Pluvialis microalgae, Phaffia rhodozyma, wild salmon, shrimp, salmon, rainbow trout and other seafood. Astaxanthin can bring many benefits to health, but not everyone can get enough, this is where the problem.

Natural astaxanthin

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. It is only the carotenoids through blood brain barrier, with true anti-aging effect and effective antioxidant is the basis of all beauty activities. Owing to its powerful antioxidant, It can effectively wrinkle anti-aging, sunscreen whitening and except for chloasma caused by age. In the prevention and treatment for age related macular degeneration and improvement of retinal function, it has good effects. All of the above can clearly be confirmed in the United States. The stability and antioxidant activity of synthetic astaxanthin also are lower than natural astaxanthin. Because of the hydroxyl (-OH) at ends of the molecule, astaxanthin can be esterification, resulting in not the same of its stability. More than 90% of natural astaxanthin is exist in ester form, and therefore more stable. Synthesic astaxanthin is the free state, therefore, the stability is not the same, must be embedded in order to stabilize. Because Left lateral structure of synthesic astaxanthin was only about 1/4, so it is only natural antioxidant of 1/4.

Production process

A method of production of chitin, astaxanthin, protein, calcium powder and biological fertilizer from shrimp shell, its production process is as follows: 1. The shrimp shell is cleaned and mechanical crushing to 5-10 mesh t. 2. The weight ratio of the shrimp shell powder and the shrimp shell was 1: 1-2, and the protease was added to the solution. According to different varieties of shrimp shell, the temperature of the enzyme solution was 30-70℃, pH value was 4-8, the time was 2-6 hours, and protease was 0.4%-1% of the shrimp shell in weight . 3. After the end of the enzyme solution, the temperature is up to 70-100℃ and then Enzyme bacteria is cool. 4. After that, adding organic solvent extraction, the weight ratio of organic solvent and shrimp shell was 1: 1-2, stirred closed fully 6-12 hours then cooling. 5. After full reaction, separate the liquid of shrimp and shrimp. 6. Shrimp liquid is divided into liquid and organic liquid.

Uses

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.

Health Benefits of Astaxanthin

(1) Astaxanthin is a powerful antioxidant. The free radical scavenging activity of astaxanthin protects lipids from peroxidation and reduces oxidative damage of LDL-cholesterol (thereby reducing arterial plaque formation), cells, cell membranes, mitochondrial membranes. Astaxanthin increases strength and endurance. (2) Astaxanthin seems to improve the immune system by increasing the number of antibody producing cells. Astaxanthin enhances antibody production by exerting actions on T-cells and T-helper cells. Astaxanthin is used to treat neurodegenerative conditions such as Alzheimer’s and Parkinson’s disease. (3) Astaxanthin protects the eyes and skin from sun radiation damage by quenching singlet and triplet oxygen. Studies with rats show that astaxanthin reduces retinal injury. (4) Studies have shown the anti-cancer effects of astaxanthin in rodents. The inhibitory effect of astaxanthin on cancer is stronger han that of beta-carotene.

Side Effects of Astaxanthin

You should also know about the side effects of astaxanthin. No toxic side-effects are related with overdose of astaxanthin. However, mild to moderate side effects are noticed with high doses of it. Some side effects include: Aplastic anemia Eye damage because of crystal formation Decreased libido Reduction in blood pressure, Enhanced skin pigmentation Gynecomastia (abnormal enlargement of breasts in men) Inhibited 5-alpha-reductase Increased hair growth Lowered eosinophil counts Parathyroid intervention Lowered serum calcium Inhibited conversion of testosterone to dihydrotestosterone

Dosage

Research has shown that the optimal dosage of astaxanthin is 4 mg per day-which relates to 200 mg of a 2% extract. It is of prime importance that when evaluating any Astaxanthin supplement that you ensure that you ingest 4 mg PER DAY-which would require 200 mg of a 2% extract-as used in our Anti-Aging Supplement. Toxicity and symptoms of high intake Astaxanthin Astaxanthin is practically non-toxic in acute animal studies at doses up to 18 grams. When tested for genotoxicity, there was no evidence for mutagenicity in Ames/Salmonella assays nor did it induce micronuclei when tested in vivo up to 2000 mg/kg in mice. There was no maternal, embryo-toxic or teratogenic effects in a teratology study in rabbits given up to 400 mg/kg over most of the gestational period. No adverse effects were noted in a one-generation reproduction study at doses up to 400 mg/kg in rats. In multiple subchronic feeding studies in rats, astaxanthin did not produce any adverse toxicological effects.

Chemical Properties

Drak-Purple Solid

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.

Uses

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

Uses

astaxanthin is an anti-oxidant. Molecularly, astaxanthin is similar to beta-carotene, but in clinical studies it appears to demonstrate stronger anti-oxidant properties, including an ability to inhibit lipid peroxidation and an anti-inflammatory capacity. It is used in cosmetics for its anti-oxidant properties, and for possible uV protection abilities. Astaxanthin is a naturally occurring pigment, part of the carotenoid group, and found in many foods. It is what provides salmon and certain crustaceans (e.g., shrimp, crab, lobster) with their reddish tint. Astaxanthin can also be synthetically produced.

Biotechnological Production

Commercial production processes are known in which astaxanthin production is performed in closed photobioreactors by Cyanotech Corporation (Hawaii). This mode of cultivation strongly improves process control, algae predation, and production, but the fermentation costs are significantly higher. These higher costs have to be compensated by high productivity levels and more efficient downstream processing in order to make a competitive product. Most of the astaxanthin available on the world market has been produced chemically since the 1950s, for example, by DSM and BASF, and the process is efficient and cost-effective. There are also microbial sources, for example, X. dendrorhous (previously described as P. rhodozyma), and the alga H. pluvialis. X. dendrorhous has been widely investigated as to its potential of astaxanthin production for salmonids. This has resulted in a race between companies in the 1980s and 1990s. Natural astaxanthin is currently available as a spray-dried powder (5–10 mg astaxanthin/g), and is supplemented to fish feed to give salmonid flesh its pink color. Another astaxanthin application is in the nutraceutical market, as astaxanthin is regarded as a potential antioxidant. With regard to production by algae, H. pluvialis is the only species commercially cultivated for astaxanthin production. This green alga is able to grow under autotrophic, heterotrophic, and mixotrophic conditions. An example of the latter is its ability to grow in the presence of acetate and light. Astaxanthin accumulates in response to stress in lipid globules of the cells.

General Description

all-trans-Astaxanthin is a ketocarotenoid, most commonly identified in marine and aquatic animals, including krill, wild salmon, rainbow trout, microalgae, shells of lobster, shrimp, seafood products, etc. It is biologically known as a vitamin A precursor, and exhibits strong antioxidant property, much higher compared to vitamin E and β-carotene. Its role in food and the medicinal industry is also well-defined.

Biochem/physiol Actions

Astaxanthin is a potent carotenoid antioxidant found in marine algae, red yeast and many other plant and animal sources. 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. In vitro studies indicate that it upregulates connexin 43 and thus, may be chemopreventive against cancer.

472-61-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (41659)  all-trans-Astaxanthin  analytical standard 472-61-7 41659-1MG 5,434.65CNY Detail
Sigma-Aldrich (41659)  all-trans-Astaxanthin  analytical standard 472-61-7 41659-5MG 24,710.40CNY Detail
Sigma (SML0982)  Astaxanthin  ≥97% (HPLC), from Haematococcus pluvailis 472-61-7 SML0982-50MG 1,113.84CNY Detail

472-61-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name astaxanthin

1.2 Other means of identification

Product number -
Other names Astaxanthin(3,3-Dihydroxy-Beta,Beta-Carotene-4,4-Dione)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:472-61-7 SDS

472-61-7Synthetic route

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

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

<5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid

<5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid

A

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

B

(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione
71772-51-5

(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione

Conditions
ConditionsYield
With sodium methylate In methanol at 0 - 25℃; for 4h;A 94.6%
B 4.2 % Chromat.
In various solvent(s) for 20h; Heating;A 97.7 % Chromat.
B 2.1 % Chromat.
C12H20O4
696647-73-1

C12H20O4

[(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

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Stage #1: C12H20O4; [(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 at 0℃; for 2h; Wittig Reaction;
Stage #2: With acetic acid In methanol; water at 20 - 75℃; for 20h; Heating / reflux;
83%
(3S,3'S)-Astaxanthin-di-(-)-camphanat

(3S,3'S)-Astaxanthin-di-(-)-camphanat

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
With sodium hydroxide In methanol; dichloromethane for 1.16667h; Ambient temperature;73%
(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial
5056-17-7

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

<5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid

<5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
70.7%
(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial
5056-17-7

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

[(2E,4E)-3-Methyl-5-((S)-2,6,6-trimethyl-3-oxo-4-phenoxymethoxycarbonyl-cyclohex-1-enyl)-penta-2,4-dienyl]-triphenyl-phosphonium; bromide

[(2E,4E)-3-Methyl-5-((S)-2,6,6-trimethyl-3-oxo-4-phenoxymethoxycarbonyl-cyclohex-1-enyl)-penta-2,4-dienyl]-triphenyl-phosphonium; bromide

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
With sodium hydride In dichloromethane; isopropyl alcohol
(3S,3'S)-astaxanthin disulfate

(3S,3'S)-astaxanthin disulfate

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
With hydrogenchloride In methanol at 40℃;
3,4,3',4'-tetrahydroxy-β,β-carotene
6094-35-5, 28082-20-4

3,4,3',4'-tetrahydroxy-β,β-carotene

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane
(S)-6-Hydroxy-3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohexen-1-on

(S)-6-Hydroxy-3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohexen-1-on

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. HBr / CH2Cl2 / 0.17 h / 0 °C
3: 94.6 percent / NaOMe / methanol / 4 h / 0 - 25 °C
View Scheme
(S)-3-((1E,3E)-5-Bromo-3-methyl-penta-1,3-dienyl)-6-hydroxy-2,4,4-trimethyl-cyclohex-2-enone

(S)-3-((1E,3E)-5-Bromo-3-methyl-penta-1,3-dienyl)-6-hydroxy-2,4,4-trimethyl-cyclohex-2-enone

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 94.6 percent / NaOMe / methanol / 4 h / 0 - 25 °C
View Scheme
3,3'-dihydroxy-β,β-carotene-4,4'-dione
7542-45-2

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

A

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

B

(3R,3'R)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione
60760-95-4

(3R,3'R)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione

C

(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione
71772-51-5

(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione

Conditions
ConditionsYield
Resolution of racemate;
(S)-2,7,11-trimethyl-13-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8,10,12-tridecahexaen-1-al
72523-68-3

(S)-2,7,11-trimethyl-13-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8,10,12-tridecahexaen-1-al

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
In ethanol for 3h; Heating / reflux;
astaxanthin radical-cation

astaxanthin radical-cation

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
With daidzein dianion In methanol; chloroform at 25℃; Thermodynamic data; Kinetics; Reagent/catalyst;
(4S)-4-acetoxy-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene

(4S)-4-acetoxy-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: E-2 / aq. phosphate buffer; acetone / 1 h / 20 - 30 °C / pH 7 / Large scale; Enzymatic reaction
2.1: pyridinium p-toluenesulfonate / toluene / 0.5 h / -5 - 5 °C / Large scale
3.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
4.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
5.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
5.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme
(4S)-4-hydroxy-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene

(4S)-4-hydroxy-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridinium p-toluenesulfonate / toluene / 0.5 h / -5 - 5 °C / Large scale
2.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
3.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
4.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
4.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme
(4S)-4-(2-methoxypropan-2-yloxy)-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene

(4S)-4-(2-methoxypropan-2-yloxy)-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
2.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
3.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
3.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme
1-(3-hydroxy-3-methyl-1,4-pentadienyl)-(4S)-4-(2-methoxypropan-2-yloxy)-3-oxo-2,6,6-trimethyl-1-cyclohexene

1-(3-hydroxy-3-methyl-1,4-pentadienyl)-(4S)-4-(2-methoxypropan-2-yloxy)-3-oxo-2,6,6-trimethyl-1-cyclohexene

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
2.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
2.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme
(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial
5056-17-7

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

1-(5-bromo-3-methyl-1,3-pentadienyl)-(4S)-4-hydroxy-3-oxo-2,6,6-trimethyl-1-cyclohexene

1-(5-bromo-3-methyl-1,3-pentadienyl)-(4S)-4-hydroxy-3-oxo-2,6,6-trimethyl-1-cyclohexene

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Stage #1: 1-(5-bromo-3-methyl-1,3-pentadienyl)-(4S)-4-hydroxy-3-oxo-2,6,6-trimethyl-1-cyclohexene With ethyloxirane; triphenylphosphine In ethyl acetate at 0 - 30℃; for 24h; Large scale;
Stage #2: (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial With ethyloxirane; 2,6-di-tert-butyl-4-methyl-phenol In isopropyl alcohol for 30h; Reflux; Inert atmosphere; Large scale;
1.53 kg
2-[2-((4RS)-4-acetoxy-3-oxo-2,6,6-trimethyl-1-cyclohexenyl)vinyl]-2-methyl-1,3-dioxolane

2-[2-((4RS)-4-acetoxy-3-oxo-2,6,6-trimethyl-1-cyclohexenyl)vinyl]-2-methyl-1,3-dioxolane

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: LAY 400-AF / aq. phosphate buffer; toluene / 24 h / 37 °C / pH 7 / Enzymatic reaction
1.2: 3 h / 50 °C
2.1: hydrogenchloride / toluene; methanol; water / 2 h / 20 - 30 °C
3.1: E-2 / aq. phosphate buffer; acetone / 1 h / 20 - 30 °C / pH 7 / Large scale; Enzymatic reaction
4.1: pyridinium p-toluenesulfonate / toluene / 0.5 h / -5 - 5 °C / Large scale
5.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
6.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
7.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
7.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme
Multi-step reaction with 7 steps
1.1: LAY 400-AF / aq. phosphate buffer; toluene / 24 h / 37 °C / pH 7 / Enzymatic reaction
2.1: hydrogenchloride / toluene; methanol; water / 2 h / 20 - 30 °C
3.1: E-2 / aq. phosphate buffer; acetone / 1 h / 20 - 30 °C / pH 7 / Large scale; Enzymatic reaction
4.1: pyridinium p-toluenesulfonate / toluene / 0.5 h / -5 - 5 °C / Large scale
5.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
6.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
7.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
7.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme
2-[2-((4S)-4-acetoxy-3-oxo-2,6,6-trimethyl-1-cyclohexenyl)vinyl]-2-methyl-1,3-dioxolane

2-[2-((4S)-4-acetoxy-3-oxo-2,6,6-trimethyl-1-cyclohexenyl)vinyl]-2-methyl-1,3-dioxolane

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogenchloride / toluene; methanol; water / 2 h / 20 - 30 °C
2.1: E-2 / aq. phosphate buffer; acetone / 1 h / 20 - 30 °C / pH 7 / Large scale; Enzymatic reaction
3.1: pyridinium p-toluenesulfonate / toluene / 0.5 h / -5 - 5 °C / Large scale
4.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
5.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
6.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
6.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme
canthaxanthin
514-78-3

canthaxanthin

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Stage #1: canthaxanthin With iodosylbenzene; sodium hydroxide In methanol at 10 - 20℃; for 12.5h; Inert atmosphere;
Stage #2: With sulfuric acid In water at 20℃; for 5h; Reagent/catalyst; Temperature; Solvent;
4.48 g
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

A

astaxanthin dipalmitate
5794-22-9

astaxanthin dipalmitate

B

(6S)-6-palmitoyloxy-3-[(all-E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone

(6S)-6-palmitoyloxy-3-[(all-E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone

Conditions
ConditionsYield
With pyridine In dichloromethane for 5h; Concentration;A 92.48%
B 0.63%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

C16H23ClO3Si

C16H23ClO3Si

astaxanthin diferulate

astaxanthin diferulate

Conditions
ConditionsYield
Stage #1: (3S,3'S)-astaxanthin; C16H23ClO3Si With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: With caesium carbonate In water; N,N-dimethyl-formamide for 2h; Inert atmosphere;
80%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

Stearoyl chloride
112-76-5

Stearoyl chloride

astaxanthin dioctadecanoate
173422-82-7

astaxanthin dioctadecanoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;80%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

astaxanthin dipalmitate
5794-22-9

astaxanthin dipalmitate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; Concentration; Reagent/catalyst; Temperature; Solvent;73%
With pyridine
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

astaxanthin didodecanoate

astaxanthin didodecanoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;73%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

n-decanoyl chloride
112-13-0

n-decanoyl chloride

[(1S)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-decanoyloxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-2-oxocyclohex-3-en-1-yl] decanoate

[(1S)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-decanoyloxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-2-oxocyclohex-3-en-1-yl] decanoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;69%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

benzoic acid
65-85-0

benzoic acid

4,4'-dioxo-β,β-carotene-3,3'-diyl dibenzoate

4,4'-dioxo-β,β-carotene-3,3'-diyl dibenzoate

Conditions
ConditionsYield
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction;59%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

p-Toluic acid
99-94-5

p-Toluic acid

4,4'-dioxo-β,β-carotene-3,3'-diyl di(4-methylbenzoate)

4,4'-dioxo-β,β-carotene-3,3'-diyl di(4-methylbenzoate)

Conditions
ConditionsYield
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction;58%
nicotinic acid
59-67-6

nicotinic acid

(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

4,4'-dioxo-β,β-carotene-3,3'-diyl di(pyridine-3-carboxylate)

4,4'-dioxo-β,β-carotene-3,3'-diyl di(pyridine-3-carboxylate)

Conditions
ConditionsYield
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction;57%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

4-Nitrophenyl chloroformate
7693-46-1

4-Nitrophenyl chloroformate

C54H58N2O12

C54H58N2O12

Conditions
ConditionsYield
Stage #1: (3S,3'S)-astaxanthin With n-butyllithium In tetrahydrofuran at -70℃; for 0.25h;
Stage #2: 4-Nitrophenyl chloroformate In tetrahydrofuran at 20℃; for 8h;
56.1%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

4,4'-dioxo-β,β-carotene-3,3'-diyl di(2-hydroxy-2-phenylethanoate)

4,4'-dioxo-β,β-carotene-3,3'-diyl di(2-hydroxy-2-phenylethanoate)

Conditions
ConditionsYield
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction;55%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

(3R,3'R)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione
60760-95-4

(3R,3'R)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione

(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione
71772-51-5

(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione

N-(all-trans-Retinoyl)-imidazole
61319-45-7

N-(all-trans-Retinoyl)-imidazole

B

(3R,3'S)-astaxanthin monoretinoate

(3R,3'S)-astaxanthin monoretinoate

Conditions
ConditionsYield
With pyridine; sodium hydride at 20℃; for 3h;A 50%
B 5%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

C108H104O22
1010099-33-8

C108H104O22

Conditions
ConditionsYield
With 4 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane at 0℃; for 2h;31%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

A

9-Z-3,3′-dihydroxy-4,4′-dione-β,β′-carotene

9-Z-3,3′-dihydroxy-4,4′-dione-β,β′-carotene

B

13-Z-3,3′-dihydroxy-4,4′-dione-β,β′-carotene

13-Z-3,3′-dihydroxy-4,4′-dione-β,β′-carotene

Conditions
ConditionsYield
With iodine-doped titanium dioxide In ethyl acetate at 70℃; for 2h; Reagent/catalyst; Temperature; Solvent;A 22.7%
B 16.9%
In acetone; Petroleum ether at 70℃; for 12h;
With I-TiO2 In ethyl acetate at 70℃; for 2h;
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

(E)-2-((3-(thiazolidin-3-yl)propyl)imino)acetic acid

(E)-2-((3-(thiazolidin-3-yl)propyl)imino)acetic acid

A

C48H64N2O5S

C48H64N2O5S

B

C56H76N4O6S2

C56H76N4O6S2

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 48h;A 10.9%
B 15.7%
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

(3S,3'S)-15,15'-cis-Astaxanthin

(3S,3'S)-15,15'-cis-Astaxanthin

Conditions
ConditionsYield
With hydrogen; Lindlar's catalyst In dichloromethane
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

(-)-methoxytrifluoromethylphenylacetyl chloride
39637-99-5

(-)-methoxytrifluoromethylphenylacetyl chloride

Conditions
ConditionsYield
With pyridine at 0℃; for 0.75h; determination of enantiomeric composition of partly racemized carotenols by converting them in to diastereomeric esters, HPLC and NMR (in the presence of Eu(fod)3 shift reagent) analysis;
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

(-)-camphanic acid chloride
39637-74-6, 104530-16-7

(-)-camphanic acid chloride

C60H76O10

C60H76O10

Conditions
ConditionsYield
With pyridine at 0℃; for 0.666667h;
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

3,4,3',4'-tetrahydroxy-β,β-carotene
6094-35-5, 28082-20-4

3,4,3',4'-tetrahydroxy-β,β-carotene

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol
(3S,3'S)-astaxanthin
472-61-7

(3S,3'S)-astaxanthin

A

(3S,3'S)-astaxanthin monosulfate

(3S,3'S)-astaxanthin monosulfate

B

(3S,3'S)-astaxanthin disulfate

(3S,3'S)-astaxanthin disulfate

Conditions
ConditionsYield
With pyridine; chlorosulfonic acid for 2.5h; Ambient temperature; Yield given;
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