Chemical Properties of Shikimic acid (CAS 138-59-0)

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)

InChI Key

JXOHGGNKMLTUBP-UHFFFAOYSA-N

Formula

C7H10O5

SMILES

O=C(O)C1=CC(O)C(O)C(O)C1

Molecular Weight¹

174.15

CAS

138-59-0

Other Names

• (-)-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid
• (-)-shikimic acid
• (3R,4S,5R)-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid
• (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid
• 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-
• 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, [3R-(3«alpha»,4«alpha»,5«beta»)]-
• 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
• Bracken fern toxic component
• L-shikimic acid
• Shikimate
• Skikimic acid

• C_p,gas : Ideal gas heat capacity (J/mol×K).
• η : Dynamic viscosity (Pa×s).
• Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
• logP_oct/wat : Octanol/Water partition coefficient.
• McVol : McGowan's characteristic volume (ml/mol).
• I_np : Non-polar retention indices.
• T_fus : Normal melting (fusion) point (K).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
ΔfusH°	31.10	kJ/mol	Joback Calculated Property
logPoct/wat	-1.516		Crippen Calculated Property
McVol	119.380	ml/mol	McGowan Calculated Property
Inp	[2036.60; 2036.60]
Inp	2036.60		NIST
Inp	2036.60		NIST
Tfus	[459.15; 460.15]	K
Tfus	460.15	K	Thermodynamic models for determination of the solubility of (-)-shikimic acid in different pure solvents and in (H2O + ethanol) binary solvent mixtures
Tfus	459.15	K	Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) Compiled value

Cheméo can also estimate Normal Boiling Point Temperature, Critical Temperature, Critical Pressure, Critical Volume, Enthalpy of formation at standard conditions, Enthalpy of vaporization at standard conditions, Standard Gibbs free energy of formation, Acentric Factor, Ionization energy, Log10 of Water solubility in mol/l for this compound, but they fall outside the models' validated range, so they are not shown here. Open the prediction tool to compute them on demand.

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[167.59; 411.31]	J/mol×K	[273.00; 1000.00]	Joback Predicted correlation
Equation			Y = A + B·T + C·T² + D·T³ + E·T⁴ Y is Cp,gas in J/mol×K, T in K
Coefficient A			-1.46500e+01
Coefficient B			7.75200e-01
Coefficient C			-4.11240e-04
Coefficient D			6.20000e-08
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	167.59	J/mol×K	273.00	Calculated Property
Cp,gas	210.87	J/mol×K	353.78	Calculated Property
Cp,gas	249.65	J/mol×K	434.56	Calculated Property
Cp,gas	284.11	J/mol×K	515.33	Calculated Property
Cp,gas	314.46	J/mol×K	596.11	Calculated Property
Cp,gas	340.88	J/mol×K	676.89	Calculated Property
Cp,gas	363.58	J/mol×K	757.67	Calculated Property
Cp,gas	382.76	J/mol×K	838.44	Calculated Property
Cp,gas	398.60	J/mol×K	919.22	Calculated Property
Cp,gas	411.31	J/mol×K	1000.00	Calculated Property

Property	Value	Unit	Temperature (K)	Source
η	[0.0011734; 0.0000110]	Pa×s	[459.65; 692.95]	Joback Predicted correlation
Equation			Y = exp(A + B/T + C·ln(T) + D·T^E) Y is η in Pa×s, T in K
Coefficient A			-2.06261e+01
Coefficient B			6.37914e+03
Coefficient C			0.00000e+00
Coefficient D			0.00000e+00
Coefficient E			0.00000e+00
Comment			Liquid phase. Joback/Reid (1987), valid from Tf to 0.7·Tc.
Temperature range, min.			459.65
Temperature range, max.			692.95
η	0.0011734	Pa×s	459.65	Calculated Property
η	0.0005594	Pa×s	485.57	Calculated Property
η	0.0002874	Pa×s	511.49	Calculated Property
η	0.0001575	Pa×s	537.42	Calculated Property
η	0.0000912	Pa×s	563.34	Calculated Property
η	0.0000554	Pa×s	589.26	Calculated Property
η	0.0000351	Pa×s	615.18	Calculated Property
η	0.0000231	Pa×s	641.10	Calculated Property
η	0.0000157	Pa×s	667.03	Calculated Property
η	0.0000110	Pa×s	692.95	Calculated Property

Similar Compounds

Find more compounds similar to Shikimic acid.

Mixtures

• Shikimic acid + Water
• Ethanol + Shikimic acid
• 1-Propanol + Shikimic acid
• 2-Propanol + Shikimic acid
• Shikimic acid + 1-Pentanol
• Shikimic acid + Heptane
• Ethanol + Shikimic acid + Water

Sources

• Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) ChEDL chemicals 1.5.2, from Bradley, J.-C.; Williams, A.; Lang, A. Jean-Claude Bradley Open Melting Point Dataset. Figshare, 2014 (CC0).
• Cheméo Relay (1.0, beta) Beta: served but experimental, data-limited and below our cross-validation release bar; the Joback value is recommended where available.
• Crippen Method
• Crippen Method
• Thermodynamic models for determination of the solubility of (-)-shikimic acid in different pure solvents and in (H2O + ethanol) binary solvent mixtures
• Joback Method
• McGowan Method
• NIST Webbook

Note: Cheméo is only indexing the data, follow the source links to retrieve the latest data. The source is also providing more information like the publication year, authors and more. Take the time to validate and double check the source of the data.
Calculated This icon marks a calculated value or equation: a prediction, not a measurement.
Compiled This icon marks a compiled value or equation: taken from a data compilation such as ChemSep, not from an original measurement report.
These property values are available through the Cheméo API. A free account gives you an access key.