D-Isomenthol

CAS# 23283-97-8

D-Isomenthol

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Chemical structure

D-Isomenthol

3D structure

Chemical Properties of D-Isomenthol

Cas No. 23283-97-8 SDF Download SDF
PubChem ID 45056 Appearance Colorless crystals
Formula C10H20O M.Wt 156.27
Type of Compound Isoprenoids Storage Desiccate at -20°C
Synonyms (+)-Isomenthol;Isomenthol
Solubility Soluble in ethanol and methanol; insoluble in water
Chemical Name (1S,2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
SMILES CC1CCC(C(C1)O)C(C)C
Standard InChIKey NOOLISFMXDJSKH-BBBLOLIVSA-N
Standard InChI InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9-,10+/m1/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.

D-Isomenthol Dilution Calculator

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D-Isomenthol Molarity Calculator

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Preparing Stock Solutions of D-Isomenthol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.3992 mL 31.9959 mL 63.9918 mL 127.9836 mL 159.9795 mL
5 mM 1.2798 mL 6.3992 mL 12.7984 mL 25.5967 mL 31.9959 mL
10 mM 0.6399 mL 3.1996 mL 6.3992 mL 12.7984 mL 15.998 mL
50 mM 0.128 mL 0.6399 mL 1.2798 mL 2.5597 mL 3.1996 mL
100 mM 0.064 mL 0.32 mL 0.6399 mL 1.2798 mL 1.5998 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 D-Isomenthol

Esters of pyromellitic acid. Part II. Esters of chiral alcohols: para pyromellitate diesters as a novel class of resolving agents and use of pyromellitates as duplicands for chiral purification.[Pubmed:18522418]

J Org Chem. 2008 Jul 4;73(13):4939-48.

Methods are presented for the preparation of pyromellitate esters of chiral terpene alcohols, including d- (3) or l-menthol (4), D-Isomenthol (7), l-borneol (8), or d- (5) or l-isopinocampheol (6). Alcoholysis of PMDA in CH2Cl2/Et3N led to the formation of monoesters (e.g., 18) or diesters (11, 12), as needed, relying on the differential reactivity of the two anhydride groups. The easily isolated para diester (11) crystallized before the meta diester (12) from HOAc. Nicotine (1, 14) was efficiently resolved as 1:1 salts with the menthyl (11a, 11b) or bornyl (11f) para diesters, prototypes of what promises to be a large class of novel resolving agents. Recrystallization of para-di-d-menthyl pyromellitate (11a) greatly improved the chiral purity of the contained d-menthol (3), an example of purification by "duplication". An alternative synthesis of specific diesters took advantage of the easily separated benzyl diesters and their derived acid chlorides (19, 21), with the benzyl esters serving as temporary blocking groups removable by catalytic hydrogenolysis. Pyromellitate tetraesters (26) were prepared by base-catalyzed transesterification of the tetraethyl ester (25). Tri- l-menthyl pyromellitate (27b) was obtained by catalytic hydrogenolysis of benzyl tri-l-menthyl pyromellitate (31b), itself prepared from the alcoholysis of benzyl pyromellitate triacid chloride (30) with l-menthol (4).

Effect of l-menthol on laryngeal receptors.[Pubmed:2022571]

J Appl Physiol (1985). 1991 Feb;70(2):788-93.

We have studied the effect of l-menthol on laryngeal receptors. Experiments have been conducted in 11 anesthetized dogs that breathed through a tracheostomy. We have recorded the activity of 23 laryngeal cold receptors and 19 mechanoreceptors. Constant flows of air, 15-50 ml/s (low) and 100-150 ml/s (high), passing for 10 s through the isolated upper airway in the expiratory direction, lowered laryngeal temperature and activated the cold receptors. This cold-induced discharge promptly ceased upon withdrawal of the airflow. Addition of l-menthol to the airflow evoked, for a similar decrease in temperature, a greater peak activation of the cold receptors than airflow alone (low flows 164%, high flows 111%); statistical significance was reached only for the lower flow. This activity outlasted the cessation of airflow by 30-120 s, even at a time when laryngeal temperature had returned to control (low flow 237%, high flow 307% of similar trials with airflow alone). Four laryngeal cold receptors were also tested with l-menthol added to a warm, humidified airflow that did not change laryngeal temperature; all of them were stimulated with a long-lasting discharge. Nine cold receptors were also tested with d-neomenthol and D-Isomenthol; both isomers stimulated the receptors. None of the 19 mechano-receptors tested was affected by l-menthol. We conclude that l-menthol constitutes a specific stimulant of laryngeal cold receptors and could provide a useful tool for the study of their reflex effects.

The effects of menthol isomers on nasal sensation of airflow.[Pubmed:3370851]

Clin Otolaryngol Allied Sci. 1988 Feb;13(1):25-9.

The effects of inhalation of L-menthol, D-Isomenthol and D-neomenthol, upon nasal resistance and sensation to airflow were investigated in 40 subjects. L-menthol caused a highly significant enhancement of nasal sensation of airflow but despite their great similarity in structure and a similar peppermint smell the isomers D-Isomenthol and D-neomenthol had no effect on nasal sensation of airflow. These findings show that L-menthol has a specific pharmacological action on nasal sensory nerve endings which is not related to its peppermint smell.

Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves.[Pubmed:16662335]

Plant Physiol. 1982 May;69(5):1013-7.

The monoterpene ketone l-menthone is specifically converted to l-menthol and l-menthyl acetate and to d-neomenthol and d-neomenthyl-beta-d-glucoside in mature peppermint (Mentha piperita L. cv. Black Mitcham) leaves. The selectivity of product formation results from compartmentation of the menthol dehydrogenase with the acetyl transferase and that of the neomenthol dehydrogenase with the glucosyl transferase. Soluble enzyme preparations, but not particulate preparations, from mature peppermint leaves catalyzed the NADPH-dependent reduction of l-menthone to both epimeric alcohols, and the two dehydrogenases responsible for these stereospecific transformations were resolved by affinity chromatography on Matrex Gel Red A. Both enzymes have a molecular weight of approximately 35,000, possess a K(m) for NADPH of about 2 x 10(-5)m, are very sensitive to inhibition by thiol-directed reagents, and are not readily reversible. The menthol dehydrogenase showed a pH optimum at 7.5, exhibited a K(m) for l-menthone of about 2.5 x 10(-4)m, and also reduced d-isomenthone to d-neoisomenthol. The neomenthol dehydrogenase showed a pH optimum at 7.6, exhibited a K(m) for l-menthone of about 2.2 x 10(-5)m, and also reduced d-isomenthone to D-Isomenthol. These stereochemically distinct, but otherwise similar, enzymes are of key importance in determining the metabolic fate of menthone in peppermint, and they are probably typical of the class of dehydrogenases thought to be responsible for the metabolism of monoterpene ketones during plant development.

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