(+)-Isopulegol

CAS# 104870-56-6

(+)-Isopulegol

2D Structure

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  • Isopulegol

    Catalog No.:BCN4974
    CAS No.:7786-67-6

Quality Control of (+)-Isopulegol

3D structure

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(+)-Isopulegol

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Chemical Properties of (+)-Isopulegol

Cas No. 104870-56-6 SDF Download SDF
PubChem ID 1268090 Appearance Oil
Formula C10H18O M.Wt 154.25
Type of Compound Monoterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1S,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
SMILES CC1CCC(C(C1)O)C(=C)C
Standard InChIKey ZYTMANIQRDEHIO-AEJSXWLSSA-N
Standard InChI InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of (+)-Isopulegol

The herbs of Mentha canadensis L.

Protocol of (+)-Isopulegol

Structure Identification
Chemcatchem, 2017.

Selectivity in the Cyclization of Citronellal Introduced by Squalene Hopene Cyclase Variants.[Reference: WebLink]

The squalene hopene cyclase from Alicyclobacillus acidocaldarius (AacSHC) is a highly efficient enzyme catalyst for stereoselective Brønsted acid catalysis.
METHODS AND RESULTS:
We engineered AacSHC to catalyze the selective Prins cyclization of citronellal. Four active site variants were identified for the diastereoselective cyclization of (S)‐citronellal to stereoisomers (−)‐iso‐isopulegol, (+)-Isopulegol and (−)‐neo‐isopulegol, respectively. The replacement of active site residues resulted in two triple variants that catalyzed the transformation of (R)‐citronellal to give the isomers (+)‐neo‐isopulegol and (−)‐isopulegol with up to >99 % de, respectively. The newly designed library of functionally diverse active site geometries exhibits high selective control during citronellal cyclization, leading exclusively to a single diastereomer of the desired isopulegol. Whereas the cyclization of citronellal with chemical catalysts was observed to produce the isopulegol isomer with the lowest energy, the reaction with AacSHC variants proceeded with higher product selectivity.
CONCLUSIONS:
The results of this study show that variants of AacSHC are excellent catalysts for the highly selective formation of isopulegol stereoisomers.

(+)-Isopulegol Dilution Calculator

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(+)-Isopulegol Molarity Calculator

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Preparing Stock Solutions of (+)-Isopulegol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.483 mL 32.4149 mL 64.8298 mL 129.6596 mL 162.0746 mL
5 mM 1.2966 mL 6.483 mL 12.966 mL 25.9319 mL 32.4149 mL
10 mM 0.6483 mL 3.2415 mL 6.483 mL 12.966 mL 16.2075 mL
50 mM 0.1297 mL 0.6483 mL 1.2966 mL 2.5932 mL 3.2415 mL
100 mM 0.0648 mL 0.3241 mL 0.6483 mL 1.2966 mL 1.6207 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on (+)-Isopulegol

Chemoenzymatic Synthesis of the Intermediates in the Peppermint Monoterpenoid Biosynthetic Pathway.[Pubmed:29979593]

J Nat Prod. 2018 Jul 27;81(7):1546-1552.

A chemoenzymatic approach providing access to all four intermediates in the peppermint biosynthetic pathway between limonene and menthone/isomenthone, including noncommercially available intermediates (-)- trans-isopiperitenol (2), (-)-isopiperitenone (3), and (+)- cis-isopulegone (4), is described. Oxidation of (+)-Isopulegol (13) followed by enolate selenation and oxidative elimination steps provides (-)-isopiperitenone (3). A chemical reduction and separation route from (3) provides both native (-)- trans-isopiperitenol (2) and isomer (-)- cis-isopiperitenol (18), while enzymatic conjugate reduction of (-)-isopiperitenone (3) with IPR [(-)-isopiperitenone reductase)] provides (+)- cis-isopulegone (4). This undergoes facile base-mediated chemical epimerization to (+)-pulegone (5), which is subsequently shown to be a substrate for NtDBR ( Nicotiana tabacum double-bond reductase) to afford (-)-menthone (7) and (+)-isomenthone (8).

One-step, stereoselective synthesis of octahydrochromanes via the Prins reaction and their cannabinoid activities.[Pubmed:29880989]

Tetrahedron Lett. 2018 Feb 28;59(9):807-810.

Novel, functionalized octahydrochromene derivatives were synthesized in a single step via the Prins reaction. Enantiomerically pure (+)-Isopulegol was reacted with benzaldehyde to stereoselectively yield the corresponding octahydro-2H-chromen-4-ol derivative containing five stereocenters. A total of 10 compounds were synthesized by altering the enantiomer of isopulegol and the substituted benzaldehyde, and the resulting enantiopure octahydrochromenes were screened in vitro against the cannabinoid receptor isoforms CB1 and CB2. Compounds containing an olefin at the C4 position [(+)-3c, (-)-3c, (-)-7c, (-)-9c and (-)-11c] of the octahydrochromene scaffold were found to exhibit reasonable displacement of [(3)H] CP55,940 from the CB receptors, whereas the corresponding hydroxy analogs [(+)-3a, (+)-3b, (-)-3a, (-)-3b and (+)-5a] had very little or no effect.

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