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138-59-0 molecular structure
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(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid

ChemBase ID: 119443
Molecular Formular: C7H10O5
Molecular Mass: 174.1513
Monoisotopic Mass: 174.05282342
SMILES and InChIs

SMILES:
C1(=C[C@H]([C@H]([C@@H](C1)O)O)O)C(=O)O
Canonical SMILES:
O[C@@H]1CC(=C[C@H]([C@H]1O)O)C(=O)O
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

Cite this record

CBID:119443 http://www.chembase.cn/molecule-119443.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
IUPAC Traditional name
(-)-shikimate
Synonyms
Shikimic acid
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid
(3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
Shikimic acid
L-Shikimic acid
NSC 59257
(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid
3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
(-)-Shikimic acid
(-)-莽草酸
CAS Number
138-59-0
EC Number
205-334-2
MDL Number
MFCD00066278
Beilstein Number
2210055
4782717
Merck Index
148480
PubChem SID
24899647
162102624
PubChem CID
8742
CHEBI ID
16119
CHEMBL
290345
Chemspider ID
8412
KEGG ID
C00493
Wikipedia Title
Shikimic_acid

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 4.103319  H Acceptors
H Donor LogD (pH = 5.5) -3.0506496 
LogD (pH = 7.4) -4.7369246  Log P -1.6400741 
Molar Refractivity 38.9603 cm3 Polarizability 15.229941 Å3
Polar Surface Area 97.99 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Methanol expand Show data source
Water expand Show data source
Apperance
Powder expand Show data source
White to Off-White Solid expand Show data source
Melting Point
~185 °C (dec.) expand Show data source
183-185°C (dec.) expand Show data source
184-188°C expand Show data source
185–187 °C expand Show data source
185-187 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -175±10°, c = 2% in H2O expand Show data source
-175 (c=2 in water) expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Storage Warning
Hygroscopic expand Show data source
RTECS
GW4600000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥97.0% (T) expand Show data source
≥99% expand Show data source
98% expand Show data source
Certificate of Analysis
Download expand Show data source
Ignition Residue
≤1% expand Show data source
Empirical Formula (Hill Notation)
C7H10O5 expand Show data source
Classification
Rare Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - S5375 external link
Biochem/physiol Actions
Biosynthetic precursor of aromatic amino acids, as well as many alkaloids and other aromatic metabolites.
包装
10 mg in autosmp vl
Sigma Aldrich - 85091 external link
Other Notes
Intermediate in the biosynthesis of aromatic amino acids 1; Preparation of derivatives 2,3
Toronto Research Chemicals - S357100 external link
Naturally occurring (-)-form is a major biosynthetic precursor of phenylalanine, tyrosine, and tryptophan and hence of the majority of plant alkaloids. It is also involved in the biosynthesis of lignin, flavonpids and other important aromatic compounds.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Evans, I.A., et al.: Nature, 250, 348 (1974)
  • • Harborne, J.B., et al.: Biosynthesis, 6, 40 (1974)
  • • Key intermediate in the biosynthesis of aromatic amino acids.
  • • Monograph: E. Haslam, Shikimic Acid, Wiley, Chichester (1993). Reviews: Chem. Rev., 65, 435 (1965); Tetrahedron, 34, 3353 (1978); Biosynthesis, 6, 40 (1980); Natural Prod. Rep., 10, 233 (1993); Synthesis, 179 (1993).
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PATENTS

PATENTS

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INTERNET

INTERNET

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