Shikimic acid

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Names

[ CAS No. ]:
138-59-0

[ Name ]:
Shikimic acid

[Synonym ]:
(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid
MFCD00066278
3,4,5-Trihydroxycyclohex-1-enecarboxylic acid
3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
(3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid
EINECS 205-334-2
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-
3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
Shikimic Acid

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
400.5±45.0 °C at 760 mmHg

[ Melting Point ]:
185-187 °C(lit.)

[ Molecular Formula ]:
C7H10O5

[ Molecular Weight ]:
174.151

[ Flash Point ]:
210.1±25.2 °C

[ Exact Mass ]:
174.052826

[ PSA ]:
97.99000

[ LogP ]:
-0.92

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.680

[ Water Solubility ]:
18 g/100 mL (20 ºC)

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GW4600000
CHEMICAL NAME :
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-
CAS REGISTRY NUMBER :
138-59-0
LAST UPDATED :
199510
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C7-H10-O5
MOLECULAR WEIGHT :
174.17
WISWESSER LINE NOTATION :
L6UTJ AVQ CQ DQ EQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4000 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
40 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
Dominant lethal test
TYPE OF TEST :
Dominant lethal test

MUTATION DATA

TYPE OF TEST :
Morphological transformation
TEST SYSTEM :
Rodent - hamster Kidney
DOSE/DURATION :
250 mg/L
REFERENCE :
TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 19,43,1983 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 40,47,1986 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 40,47,1986 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 60,1171,1976

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
GW4600000

[ HS Code ]:
29181980

Synthetic Route

Precursor & DownStream

Precursor

  • Methyl (-)-Shikimate
  • D-glucopyranose
  • methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate
  • (1R,5R,6R)-methyl 5-(benzoyloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate

DownStream

  • Methyl (-)-Shikimate
  • Oseltamivir
  • 3-Hydroxybenzoicacid
  • Phenol
  • 4-Hydroxybenzoic acid
  • 1H-Indazole
  • Methyl 3-Hydroxybenzoate
  • D-(-)-Quinic acid
  • Oseltamivir phosphate
  • 5-Azido Oseltamivir

Customs

[ HS Code ]: 2918199090

[ Summary ]:
2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

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Related Compounds

  • shikimic acid
  • shikimic acid
  • Aminoshikimic acid
  • 3-epi-shikimic acid
  • 3-Dehydroshikimic acid
  • shikimic acid acetonide