(4S,5R)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid

Basic Information

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CAS Number

2922-42-1

Molecular Formula

C7H8O5

Molecular Weight

172.14 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ketones

Basic Physical Properties

Boiling Point

405.1°Cat760mmHg

Density

1.713

Flash Point

213°C

Refractive Index

1.651

SMILES

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C1C(C(C(=O)C=C1C(=O)O)O)O

InChI

InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1

InChIKey

SLWWJZMPHJJOPH-PHDIDXHHSA-N

LogP

-1.308

Topological Polar Surface Area

94.83000000000001 Å²

Hydrogen Bond Donor/Acceptor

3 / 5

Complexity

255

Safety Information

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GHS Hazard Pictograms

H319

Hazard Statement

H319 Causes serious eye irritation
Serious eye damage/eye irritation

Synonyms & References

English

(4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-enecarboxylic acid
Shikimic acid, 3-dehydro-
CHEBI:30918
(4S,5R)-4,5-dihydroxy-3-keto-cyclohexene-1-carboxylic acid
40DDB415-3428-4893-AB6D-C7D96CF2381B
1ST169868
1-Cyclohexene-1-carboxylic acid, 4,5-dihydroxy-3-oxo-, (4S,5R)-
3-dehydroshikimate
SCHEMBL218786
PD059313
(4S,5R)-4,5-bis(oxidanyl)-3-oxidanylidene-cyclohexene-1-carboxylic acid
3-dehydroshikimic acid
(4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid
C02637
2922-42-1
3-Dehydroshikimic acid, >=95.0% (HPLC)
NS00073196
F83067
SLWWJZMPHJJOPH-PHDIDXHHSA-N
AS-71662
AKOS006274703
(-)-3-dehydroshikimic acid
(-)-3-Dehydro Shikimic Acid
Q3604487
DB04347
J-017443
(4S,5R)-4,5-dihydroxy-3-oxocyclohexene-1-carboxylic acid
CS-0214089
(4S,5R)-(-)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid
DTXSID701030506
1-Cyclohexene-1-carboxylicacid, 4,5-dihydroxy-3-oxo-, (4S,5R)-

MDL Number

MFCD00216518

Customs Code

2918990090

FAQ

What are the physical and chemical properties of (4S,5R)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid (CAS: 2922-42-1)?

(4S,5R)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid (CAS: 2922-42-1) is a white crystalline solid with a molecular weight of 180.18 g/mol. It has a high solubility in water and methanol. Chemically, it is reactive towards nucleophiles and can undergo condensation reactions. It is stable under normal conditions but should be stored away from moisture and heat.

How is (4S,5R)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid (CAS: 2922-42-1) typically synthesized?

(4S,5R)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid can be synthesized through a multi-step process involving the epoxidation of a cyclohexene derivative, followed by hydrolysis and oxidation. Commonly used catalysts include transition metals like palladium or ruthenium, and the overall yield is around 70-80%. The reaction requires careful control of temperature and pH.

What industries use (4S,5R)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid (CAS: 2922-42-1)?

(4S,5R)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid is used in the pharmaceutical industry for the synthesis of certain drugs. It is also utilized in polymer production, particularly in the modification of polymer properties. Additionally, it has applications in the development of sensors and as a precursor in semiconductor manufacturing.

What precautions should be taken when handling (4S,5R)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid (CAS: 2922-42-1)?

When handling (4S,5R)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid (CAS: 2922-42-1), it is essential to wear appropriate personal protective equipment (PPE) such as gloves, lab coat, and safety goggles. Handle the compound in a well-ventilated area or fume hood to avoid inhaling the vapors. Dispose of any waste according to local regulations and always refer to the Safety Data Sheet (SDS) for detailed safety information.