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

Basic Information

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CAS Number

138-59-0

Molecular Formula

C7H10O5

Molecular Weight

174.15 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Physical Properties

Physical State

Powder

Melting Point

185-187 °C

Boiling Point

400.5°C at 760 mmHg

Water Solubility

18 g/100 mL (20 ºC)

Flash Point

210.1 oC

Solubility

180g/l

Refractive Index

-180 ° (C=1, H2O)

Specific Rotation

-180 º (c=4, H2O 25 ºC)

SMILES

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O[C@H]1[C@H](O)[C@H](O)C=C(C(O)=O)C1

InChI

InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1

InChIKey

JXOHGGNKMLTUBP-HSUXUTPPSA-N

LogP

-1.5162

pKa

pK (14.1°) 5.19

Topological Polar Surface Area

97.99000000000001 Å²

Hydrogen Bond Donor/Acceptor

4 / 5

Complexity

222

Safety Information

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GHS Hazard Pictograms

H318

Hazard Statement

H318 Causes serious eye damage
Serious eye damage/eye irritation

Storage Conditions

2-8℃

Sensitiveness

Hygroscopic

Toxicity

LD5 i.p. in mice: 1000 mg/kg (Evans, Osman)

Synonyms & References

English

3,4,5-Trihydroxycyclohex-1-enecarboxylic acid
1-CYCLOHEXENE-1-CARBOXYLIC ACID, 3,4,5-TRIHYDROXY-, (3R,4S,5R)
3,4,5-TRIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC ACID
(-)3ALPHA,4ALPHA,5BETA-TRIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC ACID
(3R,4S,5R)-3,4,5-TRIHYDROXY-1-CYCLOHEXENECARBOXYLIC ACID
(3R,4S,5R)-3,4,5-TRIHYDROXY-CYCLOHEX-1-ENECARBOXYLIC ACID
(3R,4S,5R)-3,4,5-TRIHYDROXYL-1-CYCLOHEXENE-1-CARBOXYLIC ACID
(3R,4S,5R)-TRIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC ACID
L-SHIKIMIC ACID
(-)-SHIKIMIC ACID
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, [3R-(3alpha,4alpha,5beta)]-
Bracken fern toxic component
Shikimate
Skikimic acid
Kava Kava Extract
3,4,5-Trihydroxy-1-Cyclohexene-1-Carboxylic Acid (Shikimic acid)
Shikimic
(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
Shikimic acid
(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid
SHIKIMIC ACID(RG)
(3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid
(3R,4S,5R)-(?)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
(3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
[ "" ]
NSC 59257
sikimic acid
Shikimik Acid
(3R,4S,5R)-3,4,5-TRIHYDROXYCYCLOHEX-1-ENE-1-CARBOXYLIC ACID

MDL Number

MFCD00066278

Customs Code

29181980

FAQ

What is (3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid (CAS: 138-59-0)?

(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid, with CAS number 138-59-0, is a cyclic organic compound containing three hydroxyl groups and a carboxylic acid group. It is a key intermediate in the synthesis of various pharmaceuticals and bioactive molecules. The compound is known for its stereochemistry, with specific configurations at the R and S centers, contributing to its biological activity and reactivity in chemical reactions.

What are the main uses of (3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid (CAS: 138-59-0)?

(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid, CAS 138-59-0, is primarily used in pharmaceutical research for the development of drugs targeting metabolic disorders. It also serves as a building block in the synthesis of natural products and organic compounds. Its unique structure makes it valuable in biochemical studies and for creating derivatives with specific functional properties.

Is (3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid (CAS: 138-59-0) safe?

(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid, CAS 138-59-0, is generally considered safe when handled properly. However, it may cause skin and eye irritation. Safety standards recommend using personal protective equipment (PPE) such as gloves and goggles. Proper ventilation and adherence to standard chemical handling protocols are essential to ensure safe usage.

How should (3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid (CAS: 138-59-0) be stored?

(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid, CAS 138-59-0, should be stored in a cool, dry, and dark place to maintain stability. It is best kept in a sealed container away from moisture and air. Storage at temperatures below 25°C is recommended. Avoid exposure to light and ensure proper labeling to prevent contamination or misuse.