VERBENOL

VERBENOL

Sample Description:

Molecular Formula: C10H16O Molecular Weight: 152.233 InChI= 1/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3 IUPAC Name:  4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol CAS Number: 18881-04-4 PubChem: 61126 NMRShiftDB: 10021322 Spectrometer: Varian INOVA 500 MHz Solvent: CDCl3  Sample Concentration: 8 mg

Properties calculated from structure

Property	Value
Formula	C10H16O
Weight	152.233 [g/mol]
Complexity	214.91
XLogP	2.12
TPSA	20.23
#HDonors	1
#HAcceptors	1
Gibbs Energy	-42.9 [kcal/mol]
1H NMR spectrum	Predict NMR spectrum (requires installed Java plugin) Predict NMR spectrum (requires HTML5 compatible browser)
13C NMR spectrum	Predict NMR spectrum (requires HTML5 compatible browser)
Isotopic distribution	Predict Isotopic distribution

1D Proton Spectrum (TMS Resonances Subtracted):

2D HMQC Spectrum:

Determined HMQC Correlations:

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

The correct structure is at position 1.

 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.892462 (   61126)    2: 0.792875 (  421322)    3: 0.786969 (  118088)
    4: 0.782868 (  433073)    5: 0.782421 (  556905)    6: 0.776775 (  247518)
    7: 0.775072 (  282018)    8: 0.774000 (   72421)    9: 0.773790 (   91238)
   10: 0.773789 (  247514)
   

2D Phase Sensitive HMBC Spectrum:

AssembleIt HSQC (HMQC) & HMBC Derived Carbon-Carbon Correlations:

AssembleIt Derived Structure With NMRgraph Added Likely Oxygen Atoms:

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

MASS SPECTRUM

Comments:

Verbenol is a monoterpenoid pheromone.

The verbenol datasets were our first application of using indirect detection spectra. We used to base structure elucidations on a 1D carbon and a 2D INADEQUATE spectrum. Indirect detection methods gain an order of magnitude in sensitivity. But we continued to use the 1D carbon spectrum which is the least sensitive spectrum by now. Eliminating it completes our goal of indirect detection. Several insights result:

It greatly simplifies the structure elucidation when all spectra are acquired with consistent referencing (not the case for this sample). The next best approach is to use the 1D carbon spectrum to adjust the carbon referencing of all spectra. Here it was necessary to use the exhaustive HSQC and HMBC F1 mapping results for referencing corrections. This is tedious and acquiring datasets with consistent referencing is preferable.

Strong ridges at the TMS (0 ppm) and the three methyl carbon frequencies show in the regular HMBC. Adjustment of the single "Ridge" parameter excludes ridge misinterpretations as shown. It would be preferable to acquire this spectrum with Pulse Field Gradient support to simplify the spectral analysis.






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