Menthol
NMRanalyst Sample Application
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Sample Description:

 Molecular Formula: C10H20O
Molecular Weight: 156.265
InChI= 1/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3
IUPAC Name:  2-Isopropyl-5-methylcyclohexanol
CAS Number: 89-78-1
PubChem: 1254
NMRShiftDB: 10008950
Spectrometer: Varian INOVA 500 MHz
Solvent: CDCl3
Sample Concentration: 2 mg
Applications: Topical analgesic and antipruritic
Provided by:  Dr. Dimitris Argyropoulos, Varian Deutschland GmbH

*.fid/text file specifies: Menthol... 2 mg in CDCl3
*.fidnpntswrfp-rflnisw1rfp1-rfl1time
PROTON872242302.29-66.7617 s
CARBON32768819212588.51-10.345 h 14 m
gDQF-COSY102422302.82-67.032562302.29-66.7631 m
gHMBC102482302.82-67.0325612567.82059 m
gHSQC92022302.82-67.0325612566.760.5325 m


1D Proton Spectrum:

1D Proton Spectrum


1D Carbon Spectrum (Deuterated Solvent Resonances Subtracted):

1D Carbon Spectrum


 

Automated VerifyIt Proton Assignments:

Proton Assignments
 

Automated VerifyIt Carbon Assignments:

Carbon Assignments

Top 10 FindIt Molecular Structures Consistent With Molecular Formula and Proton Resonances:

The correct structure is at position 8.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.980098 (  549904)    2: 0.978656 (  228304)    3: 0.978113 (  220207)
    4: 0.977428 (  118129)    5: 0.976737 (  574674)    6: 0.976361 (   62350)
    7: 0.976332 ( 1797950)    8: 0.976110 (    1254)    9: 0.974860 (  545293)
   10: 0.974712 (   91338)
			

Top 10 FindIt Molecular Structures Consistent With Proton and Carbon Resonances:

The correct structure is at position 1.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.944837 (    1254)    2: 0.926940 ( 1597048)    3: 0.920149 ( 4418301)
    4: 0.919076 (   86798)    5: 0.918728 ( 6454875)    6: 0.917544 (   56224)
    7: 0.915304 (  375777)    8: 0.914156 (  558050)    9: 0.913513 ( 1636096)
   10: 0.912965 (  560763)
			

2D Multiplicity-Edited HSQC Spectrum:

2D Multiplicity-Edited HSQC Spectrum

Determined HSQC Correlations:

Determined HSQC Correlations

Top 10 FindIt Molecular Structures Consistent With Proton and Protonated Carbon (HSQC) Resonances:

The correct structure is at position 1.

FindIt Structures

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.943527 (    1254)    2: 0.938413 (  558259)    3: 0.935518 ( 1391551)
    4: 0.932191 (  360318)    5: 0.929882 (  520673)    6: 0.929349 ( 2755306)
    7: 0.927448 (  586745)    8: 0.926733 (  235854)    9: 0.924183 ( 1597048)
   10: 0.922191 (  583664)
			

2D DQF-COSY Spectrum:

2D DQF-COSY Spectrum

AssembleIt HSQC & DQF-COSY Derived Carbon-Carbon Correlations:

AssembleIt HSQC & DQF-COSY Derived Correlations

2D HMBC Spectrum:

2D HMBC Spectrum

AssembleIt HSQC, HMBC & DQF-COSY Derived Correlations:

AssembleIt Derived Correlations

AssembleIt Derived Structure With NMRgraph Added Likely Oxygen Atoms:

AssembleIt Derived Structure   Most likely structure (out of 4 possible ones) by agreement with carbon chemical shift prediction

Comments:

HSQC Detail

For FindIt, the correct structure is identified using proton and carbon, as well as proton and protonated carbon analysis results.

For the complete structure elucidation, the challenge are three proton frequencies (1.004, 0.955, 0.939 ppm) correlating in the HSQC with two carbons each. See the shown HSQC expansion. Ambiguities detected in the assignments of DQF-COSY and HSQC correlations are communicated to the structure generation. So all structures in agreement with ambiguous assignments are duly considered.


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