Record Information
Version1.0
Creation date2015-10-09 22:31:25 UTC
Update date2017-01-19 02:36:29 UTC
FoodComEx IDPC000590
FoodDB RecordFDB003991
Chemical Information
NameShikimic acid
DescriptionShikimic acid, also known as shikimate or acid, shikimic, belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5. A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). Shikimic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Shikimic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Shikimic acid has been detected, but not quantified in, several different foods, such as barley, macadamia nuts, nutmegs, winter squash, and borages. This could make shikimic acid a potential biomarker for the consumption of these foods.
CAS Number138-59-0
Structure
Thumb
Synonyms
SynonymSource
(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidbiospider
(-)-Shikimatebiospider
(-)-Shikimic acidbiospider
(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-ene carboxylic acidbiospider
[3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
[3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidChEBI
[3R-(3α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylateGenerator
[3R-(3α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidbiospider
3,4,5-Trihydroxy-1-cyclohexenecarboxylateGenerator
3,4,5-Trihydroxy-1-cyclohexenecarboxylic acidbiospider
3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acidChEBI
3α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylateGenerator
3α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
L-Shikimatebiospider
L-Shikimic acidbiospider
Shikimatebiospider
Shikimic acidbiospider
SkikimateHMDB
Skikimic acidHMDB
Chemical FormulaC7H10O5
IUPAC name(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
InChI IdentifierInChI=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
InChI KeyJXOHGGNKMLTUBP-HSUXUTPPSA-N
Isomeric SMILESO[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O
Average Molecular Weight174.1513
Monoisotopic Molecular Weight174.05282343
Chemical Taxonomy
Description Belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentShikimic acids and derivatves
Alternative Parents
Substituents
  • Shikimic acid or derivatives
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water Solubility150 mg/mL at 21 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point186 oC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 500 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci G934
AKSci J10551
MetaSci HMDB0003070
Sigma-Aldrich HMDB0003070
Toronto Research Chemicals S357100