Shikimic acid

Structural formula

• Numbering system
• Physical property data
• Toxicological data
• Ecological data
• Molecular structure data
• Computing chemical data
• More
  • Properties and Stability
  • Storage method
  • Synthesis method
  • Purpose

Numbering system

CAS number:138-59-0

MDL number:MFCD00066278

EINECS number:205-334-2

RTECS number:GW4600000

BRN number:4782717

PubChem number:24899647

Physical property data

1. Properties: Colorless or white needle-like crystals.

2. Solubility: Solubility in water at 20ºC is 18%, slightly soluble in ethanol and ether, almost insoluble in chloroform and benzene.

3. Boiling point (ºC): 400.5

4. Melting point (ºC): 185~187

5. Flash point (ºC): 210.1

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6. Relative density (d²⁰₄₎ : 1.725

Toxicological data

Acute toxicity data:

Mouse intraperitoneal LD: 1 mg/kg

Tumorigenicity data:

Mouse oral TDLo: 4000mg/kg

Mouse abdominal cavity TDLo: 400mg/kg

Mutagenicity data:

Mouse abdominal cavity dominant lethality test: 1000mg/kg

Oral dominant lethality test in mice: 3200mg/kg

Morphological transformation test in hamster kidney: 250mg/L

Ecological data

None

Molecular structure data

Molecular property data:

1. Molar refractive index: 38.14

2. Molar volume (cm³/mol): 100.9

3. Isotonic specific volume (90.2K): 331.7

4. Surface tension (3.0 dyne/cm): 116.6

5. Polarizability (0.5 10^-24cm³): 15.12

Compute chemical data

1. Hydrophobic parameter calculation reference value (XlogP): -1.7

2. Number of hydrogen bond donors: 4

3. Number of hydrogen bond acceptors: 5

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4. Number of rotatable chemical bonds: 1

5. Number of tautomers:

6. Topological molecular polar surface area (TPSA): 98

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7. Number of heavy atoms: 12

8. Surface charge: 0

9. Complexity: 222

10. Number of isotope atoms : 0

11. Determine the number of atomic stereocenters: 3

12. Uncertain number of atomic stereocenters: 0

13. Determine the chemical bond configuration Number of centers: 0

14. Number of uncertain chemical bond stereocenters: 0

15. Number of covalent bond units: 1

Properties and stability

1. Hygroscopic. Can sublimate

2. Exists in tobacco leaves.

Storage method

It should be sealed with argon and stored in a cool, dry place.

Synthesis method

Shikimic acid is derived fromA monomeric compound extracted from the medicinal star anise.

Purpose

Shikimic acid affects the metabolism of arachidonic acid, inhibits platelet aggregation, inhibits arterial and venous thrombosis and cerebral thrombosis, and has anti-inflammatory and analgesic effects. It can also be used as an antiviral and anticancer drug intermediate. This product is mostly used as a pharmaceutical intermediate. It has certain irritation and should not be used directly. Organic Synthesis