34995-77-2

Basic information

• Product Name: tetrahydro-alpha,alpha,5-trimethyl-5-vinylfuran-2-methanol
• Synonyms: tetrahydro-alpha,alpha,5-trimethyl-5-vinylfuran-2-methanol;(E)-linalooloxide,(E,E)-2-methyl-2vinyl-5-(2-hydroxy-2-propyl)tetrahydrofuran,trans-linaloolfuranoxide;5-ethenyltetrahydro-.alpha.,.alpha.,5-trimethyl-, trans-2-Furanmethanol;alpha,5-trimethyl- 5-ethenyltetrahydro- alph trans-2-furanmethanol;(E)-Furanoid linalool oxide;Linalool oxide A;Linalool oxide II;rel-1-[[(2R*,5R*)-5-Methyl-5-vinyltetrahydrofuran]-2-yl]-1-methylethanol
• CAS NO: 34995-77-2
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.24872
• EINECS: 252-312-3
• Mol File: 34995-77-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 222.6°Cat760mmHg
• Flash Point: 75.4°C
• Appearance: /
• Density: 1.023g/cm³
• Vapor Pressure: 0.0205mmHg at 25°C
• Refractive Index: 1.519
• PKA: 14.57±0.29(Predicted)
• CAS DataBase Reference: tetrahydro-alpha,alpha,5-trimethyl-5-vinylfuran-2-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: tetrahydro-alpha,alpha,5-trimethyl-5-vinylfuran-2-methanol(34995-77-2)
• EPA Substance Registry System: tetrahydro-alpha,alpha,5-trimethyl-5-vinylfuran-2-methanol(34995-77-2)

Safety Data

• Hazardous Substances Data: 34995-77-2(Hazardous Substances Data)

Usage

General Description

Tetrahydro-alpha, alpha, 5-trimethyl-5-vinylfuran-2-methanol, also known as Civamide, is a chemical that has been studied for its potential medicinal properties. It is derived from resiniferatoxin, a compound found in the resin of the cactus-like Euphorbia plant. Civamide has been found to have analgesic and anti-inflammatory effects, and there is ongoing research into its potential use as a pain relief medication, particularly for conditions such as arthritis and neuropathic pain. It is also being studied for its potential applications in cancer treatment and as a topical analgesic for pain relief. Additionally, Civamide has been investigated for its potential use in weight loss and metabolic disorder treatment. Overall, Civamide shows promise as a versatile compound with potential medical and therapeutic applications.

InChI:InChI=1/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3/t8-,10+/m0/s1

Upstream product

• 128344-89-8 anti-N-<1-(5-ethenyltetrahydro-5-methylfuran-2-yl)-1-methylethoxy>-2,2,6,6-tetramethylpiperidine 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 128344-89-8 syn-N-<1-(5-ethenyltetrahydro-5-methylfuran-2-yl)-1-methylethoxy>-2,2,6,6-tetramethylpiperidine 
• 40036-54-2 (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol 
• 106-24-1 Geraniol 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 85217-73-8 (Z)-3,7-dimethylocta-2,6-dien-1-yl methyl carbonate 
• 106-25-2 Nerol 
• 188579-26-2 Carbonic acid (E)-6,7-dihydroxy-3,7-dimethyl-oct-2-enyl ester ethyl ester 

Relevant articles and documents

One-pot synthesis at room temperature of epoxides and linalool derivative pyrans in monolacunary Na7PW11O39-catalyzed oxidation reactions by hydrogen peroxide

In this work, we describe a new one-pot synthesis route of valuable linalool oxidation derivatives (i.e., 2-(5-methyl-5-vinyltetrahydrofuran-2-yl propan-2-ol) (1a)), 2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran-3-ol (1b) and diepoxide (1c), using a green oxidant (i.e., hydrogen peroxide) under mild conditions (i.e., room temperature). Lacunar Keggin heteropolyacid salts were the catalysts investigated in this reaction. Among them, Na7PW11O39 was the most active and selective toward oxidation products. All the catalysts were characterized by FT-IR, TG/DSC, BET, XRD analyses and potentiometric titration. The main reaction parameters were assessed. Special attention was dedicated to correlating the composition and properties of the catalysts and their activity.

Fungal biotransformation of (±)-linalool

The biotransformation of (±)-linalool was investigated by screening 19 fungi. Product accumulation was enhanced by substrate feeding and, for the first time, lilac aldehydes and lilac alcohols were identified as fungal biotransformation byproduct using SPME-GC-MS headspace analysis. Aspergillus niger DSM 821, Botrytis cinerea 5901/02, and B. cinerea 02/FBII/2.1 produced different isomers of lilac aldehyde and lilac alcohol from linalool via 8-hydroxylinalool as postulated intermediate. Linalool oxides and 8-hydroxylinalool were the major products of fungal (±)-linalool biotransformations. Furanoid trans-(2R,5R)- and cis-(2S,5R)-linalool oxide as well as pyranoid trans-(2R,5S)- and cis-(2S, 5S)-linalool oxide were identified as the main stereoisomers with (3S,6S)-6,7-epoxylinalool and (3R,6S)-6,7-epoxylinalool as postulated key intermediates of fungal (±)-linalool oxyfunctionalization, respectively. With a conversion yield close to 100% and a productivity of 120 mg/L·day linalool oxides, Corynespora cassiicola DSM 62485 was identified as a novel highly stereoselective linalool transforming biocatalyst showing the highest productivity reported so far.

Diastereoselective titanocene-catalyzed oxidative cyclization of bishomoallylic alcohols

Bishomoallylic alcohols are converted in good yields and diastereoselectivity into tetrahydrofuranols and tetrahydropyranols by Cp2TiCl2/t-butyl hydroperoxide/activated 4? molecular sieves system.