Atractyloside A

Basic Information

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CAS Number

126054-77-1

Molecular Formula

C21H36O10

Molecular Weight

448.5 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ketones

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Surfactants Anionic Surfactants

Polymers and Plastics Thermoplastics Polyolefins

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Physical State

Powder

Solubility

Methanol,Water,DMSO

SMILES

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OC[C@H]1O[C@@H](OC([C@@H]2CC[C@]([C@@H]3[C@@H](C2)[C@](C)(O)C(=O)C3)(O)CO)(C)C)[C@@H]([C@H]([C@@H]1O)O)O

InChI

InChI=1S/C21H36O10/c1-19(2,31-18-17(27)16(26)15(25)13(8-22)30-18)10-4-5-21(29,9-23)12-7-14(24)20(3,28)11(12)6-10/h10-13,15-18,22-23,25-29H,4-9H2,1-3H3/t10-,11-,12+,13-,15-,16+,17-,18+,20+,21+/m1/s1

InChIKey

QNBLVYVBWDIWDM-BSLJOXIBSA-N

LogP

-1.9387999999999965

Topological Polar Surface Area

177.14 Å²

Hydrogen Bond Donor/Acceptor

7 / 10

Complexity

671

Safety Information

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Storage Conditions

-20℃

Synonyms & References

English

Atractyloside A
(1S,3aβ,8aα)-1-Methyl-1α,4α-dihydroxy-4-(hydroxymethyl)-7β-[1-methyl-1-(β-D-glucopyranosyloxy)ethyl]decahydroazulene-2-one
[(1β,5α)-4β-Methyl-4α,10,14-trihydroxy-3-oxo-5-demethylambrosan-11-yl]β-D-glucopyranoside
(1S,3aS,4R,7R,8aR)-7-[1-(beta-D-Glucopyranosyloxy)-1-methylethyl]octahydro-1,4-dihydroxy-4-(hydroxymethyl)-1-methyl-2(1H)-azulenone
2(1H)-Azulenone, 7-[1-(b-D-glucopyranosyloxy)-1-methylethyl]octahydro-1,4-dihydroxy-4-(hydroxy...
2(1H)-Azulenone, 7-[1-(b-D-glucopyranosyloxy)-1-methylethyl]octahydro-1,4-dihydroxy-4-(hydroxymethyl)-1-methyl-,(1S,3aS,4R,7R,8aR)-
(+)-(1S,4S,4aR,8aS)-4-((3S)-3-hydroxy-3-methyl-4-pentenyl)-4a,8,8-trimethyl-3-methylenedecahydro-1-naphthalenol
(1S,4S,4aR,8aS)-4-[(3S)-3-Hydroxy-3-methylpent-4-enyl]-4a,8,8-trimethyl-3-methylenedecahydronaphthalen-1-ol
[(1S,4R,4aR,8aS)-4-[(3S)-3-acetyloxy-3-methylpent-4-enyl]-4a,8,8-trimethyl-3-methylidene-2,4,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
LARIXOL ACETATE
2-[(3S,3aR,5R,8R,8aS)-3,8-Dihydroxy-8-(hydroxymethyl)-3-methyl-2- oxodecahydro-5-azulenyl]-2-propanyl β-D-glucopyranoside

MDL Number

MFCD16621069

FAQ

What are the physical and chemical properties of Atractyloside A (CAS: 126054-77-1)?

Atractyloside A (CAS: 126054-77-1) is a crystalline compound with a molecular weight of approximately 428.35 g/mol. It is only slightly soluble in water and ethanol, but soluble in methanol. Atractyloside A is reactive towards acidic conditions, particularly in the presence of hydrochloric acid. It is stable under neutral and basic conditions but should be stored in a desiccator to avoid moisture absorption.

How is Atractyloside A (CAS: 126054-77-1) typically synthesized?

Atractyloside A (CAS: 126054-77-1) is typically synthesized through semi-synthetic methods from natural sources, such as the roots of Atractylodes macrocephala. The synthesis involves a series of enzymatic and chemical transformations, including hydroxylation and glycosylation steps. Commonly used catalysts include enzymes like β-glucosidase and hydrogenation catalysts. The overall yield is moderate, around 10-20%, with high purity achievable through column chromatography.

What industries use Atractyloside A (CAS: 126054-77-1)?

Atractyloside A (CAS: 126054-77-1) is primarily used in the pharmaceutical industry due to its potential medicinal properties. It has shown promise in the treatment of diabetes, cardiovascular diseases, and certain types of cancer. Additionally, it finds applications in the food industry as a potential antioxidant and in the development of new sensors and semiconductors.

What precautions should be taken when handling Atractyloside A (CAS: 126054-77-1)?

When handling Atractyloside A (CAS: 126054-77-1), it is essential to wear appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. Work should be conducted in a fume hood due to its reactivity towards acids. Spills should be immediately cleaned up using absorbent materials and disposed of according to local regulations. Always refer to the Safety Data Sheet (SDS) for detailed handling and safety information.