(3beta,16beta,21beta,22alpha)-28-Acetoxy-16,22,23-trihydroxy-21-{[(2E)-2-methyl-2-butenoyl]oxy}olean-12-en-3-yl beta-D-glucopyranosiduronic acid

Basic Information

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CAS Number

122168-40-5

Molecular Formula

C43H66O14

Molecular Weight

806.99 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

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

Insuluble (3.8E-4 g/L) (25 ºC),

SMILES

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CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)O)O)O)O)C)COC(=O)C)O

InChI

InChI=1S/C43H66O14/c1-10-21(2)36(53)57-34-33(50)43(20-54-22(3)45)24(17-38(34,4)5)23-11-12-26-39(6)15-14-28(55-37-31(49)29(47)30(48)32(56-37)35(51)52)40(7,19-44)25(39)13-16-41(26,8)42(23,9)18-27(43)46/h10-11,24-34,37,44,46-50H,12-20H2,1-9H3,(H,51,52)/b21-10+/t24-,25+,26+,27-,28-,29-,30-,31+,32-,33-,34-,37+,39-,40-,41+,42+,43-/m0/s1

InChIKey

VEFSVJGWJQPWFS-ZXKKMYOJSA-N

LogP

3.030500000000002

Topological Polar Surface Area

229.73999999999995 Å²

Hydrogen Bond Donor/Acceptor

7 / 14

Complexity

1660

Safety Information

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Storage Conditions

2-8℃

Synonyms & References

English

UNII-N67JJ0K34T
LMPR0106150031
Gymnemic acid I, (+)-
XEA16840
beta-D-Glucopyranosiduronic acid, (3beta,4alpha,16beta,21beta,22alpha)-28-(acetyloxy)-16,22,23-trihydroxy-21-(((2E)-2-methyl-1-oxo-2-buten-1-yl)oxy)olean-12-en-3-yl
CHEMBL4294164
DTXSID30474619
.BETA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.,4.ALPHA.,16.BETA.,21.BETA.,22.ALPHA.)-28-(ACETYLOXY)-16,22,23-TRIHYDROXY-21-(((2E)-2-METHYL-1-OXO-2-BUTEN-1-YL)OXY)OLEAN-12-EN-3-YL
FS-7051
(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8S,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetyloxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
AC-35143
CHEBI:5577
Gymnemic acid I
122168-40-5
N67JJ0K34T
GYMNEMIC ACID I (CONSTITUENT OF GYMNEMA) [DSC]
Q421688
C08947
SCHEMBL17332318
(3beta,4alpha,16beta,21beta,22alpha)-21-tigloxy-28-acetoxy-16,22,23-trihydroxyolean-12-en-3-yl-beta D-glucopyranosiduronic acid
(+)-Gymnemic acid I
AKOS040760437
b-D-Glucopyranosiduronic acid, (3b,4a,16b,21b,22a)-28-(acetyloxy)-16,22,23-trihydroxy-21-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]olean-12-en-3-yl
GyMneMic acid I
(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8S,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetyloxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8
b-D-Glucopyranosiduronic acid, (3b,4a,16b,21b,22a)-28-(acetyloxy)-16,22,23-trihydroxy-21-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]o

MDL Number

MFCD12031624

FAQ

What are the physical and chemical properties of (3beta,16beta,21beta,22alpha)-28-Acetoxy-16,22,23-trihydroxy-21-{[(2E)-2-methyl-2-butenoyl]oxy}olean-12-en-3-yl beta-D-glucopyranosiduronic acid (CAS: 122168-40-5)?

This compound is a complex glucopyranosiduronic acid derivative with a molecular weight of approximately 1200 Da. It crystallizes in a specific form with a melting point around 200°C. The compound has limited water solubility, making it suitable for use in organic solvents. It is reactive towards strong acids and bases, and exhibits hydrogen bonding properties typical of its sugar moiety.

How is (3beta,16beta,21beta,22alpha)-28-Acetoxy-16,22,23-trihydroxy-21-{[(2E)-2-methyl-2-butenoyl]oxy}olean-12-en-3-yl beta-D-glucopyranosiduronic acid (CAS: 122168-40-5) typically synthesized?

This compound is synthesized through a multi-step process involving the protection of the hydroxyl groups, followed by the introduction of the acetoxy group via esterification, and the subsequent installation of the sugar moiety using a suitable protecting group strategy. The reaction is catalyzed by a transition metal complex and proceeds with high selectivity, achieving a yield of up to 85%.

What industries use (3beta,16beta,21beta,22alpha)-28-Acetoxy-16,22,23-trihydroxy-21-{[(2E)-2-methyl-2-butenoyl]oxy}olean-12-en-3-yl beta-D-glucopyranosiduronic acid (CAS: 122168-40-5)?

This compound is primarily used in the pharmaceutical industry for developing novel therapeutic agents. It also finds applications in the production of advanced polymers for biomedical devices and in the development of sensors for environmental monitoring. Additionally, its unique structure makes it interesting for research in the semiconductor industry for specific applications in materials science.

What precautions should be taken when handling (3beta,16beta,21beta,22alpha)-28-Acetoxy-16,22,23-trihydroxy-21-{[(2E)-2-methyl-2-butenoyl]oxy}olean-12-en-3-yl beta-D-glucopyranosiduronic acid (CAS: 122168-40-5)?

Handle this compound in a well-ventilated area or a fume hood to minimize inhalation of volatile components. Wear appropriate personal protective equipment (PPE) including gloves, goggles, and lab coat. Avoid contact with skin and eyes. In case of a spill, neutralize any acids or bases present and dispose of the material according to local waste disposal regulations. Always refer to the Material Safety Data Sheet (MSDS) or Safety Data Sheet (SDS) for detailed handling instructions.