19889-94-2

Basic information

• Product Name: [1R-(1alpha,2alpha,3beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol
• Synonyms: [1R-(1alpha,2alpha,3beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol;(1α,5α)-2α,6,6-Trimethylbicyclo[3.1.1]heptane-3β-ol;Pinocampheol;Einecs 243-403-9
• CAS NO: 19889-94-2
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.24932
• EINECS: 243-403-9
• Mol File: 19889-94-2.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 217°C at 760 mmHg
• Flash Point: 84.4°C
• Appearance: /
• Density: 0.96g/cm³
• Vapor Pressure: 0.0292mmHg at 25°C
• Refractive Index: 1.484
• CAS DataBase Reference: [1R-(1alpha,2alpha,3beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: [1R-(1alpha,2alpha,3beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol(19889-94-2)
• EPA Substance Registry System: [1R-(1alpha,2alpha,3beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol(19889-94-2)

Safety Data

• Hazardous Substances Data: 19889-94-2(Hazardous Substances Data)

Usage

General Description

[1R-(1alpha,2alpha,3beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol, also known as 3-alpha-Perillyl alcohol (POH), is a naturally occurring monocyclic monoterpene that is found in the essential oils of many plants such as lavender, peppermint, and sage. It is a colorless liquid with a pleasant citrus-like odor. POH has been studied for its potential anticancer, antibacterial, antifungal, and anti-inflammatory properties. It has shown promise as a potential therapeutic agent in the treatment of various types of cancer and has been investigated for its potential use in chemotherapy and other cancer treatments. Additionally, it has also demonstrated antimicrobial and anti-inflammatory effects, making it a compound of interest for potential pharmaceutical and medicinal applications.

InChI:InChI=1/C10H18O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h6-9,11H,4-5H2,1-3H3/t6-,7-,8+,9-/m0/s1

Upstream product

• 1686-14-2 (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane 
• 7785-26-4 (-)-α-pinene 
• 110-82-7 cyclohexane 
• 19894-98-5 6,6-dimethyl-2-methylene-bicyclo[3.1.1]heptan-3-ol 
• 99493-12-6 B-crotyldiisopinocampheylborane 
• 344796-28-7 (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methyl-pentanal 
• 1196-00-5 (-)-isopinocampheol 
• 64-17-5 ethanol 
• 18492-59-6 (+)-pinocamphone 
• 24041-60-9 (+)-isopinocampheol 
• 108-88-3 toluene 
• 2734-31-8 (1R,2R,3S,5S)-(+)-neoisopinocampheol 
• 18358-53-7 pinocamphone 
• 498-66-8 norborn-2-ene 

Downstream Products

• 14575-93-0 isopinocamphone 
• 14575-99-6 phthalic acid mono-((1S:2S:3S)-pinanyl-⁽³⁾-ester) 
• 99-87-6 4-methylisopropylbenzene 
• 39166-57-9 (1R:2S:3S)-3-Acetoxy-pinan 
• 18358-53-7 pinocamphone 
• 497-36-9 Norborneol 
• 29342-53-8 norbornyl chloride 
• 117227-80-2 isopinocampheyl chloride 
• 39166-57-9 (+)-isopinocampheyl acetate 
• 14575-90-7 isopinocamphyl tosylate 
• 473-62-1 trans-pinocamphone 

Relevant articles and documents

Synthesis and Configuration of Neomaclafungin A

The relative and absolute configuration of neomaclafungins were impossible to establish by spectroscopic analyses alone because of the lack of exploitable 1H-1H couplings and nOes between the upper and the lower subunits. This very difficult task now is finally completed by an enantioselective total synthesis of neomaclafungin A (revised) and its diastereomer (reported). The results also provided a key reference for the complete structures for other neomaclafungins and the long-known closely related natural product maclafungin.

Biology-oriented synthesis of a withanolide-inspired compound collection reveals novel modulators of hedgehog signaling

Biology-oriented synthesis employs the structural information encoded in complex natural products to guide the synthesis of compound collections enriched in bioactivity. The trans-hydrindane dehydro-δ-lactone motif defines the characteristic scaffold of the steroid-like withanolides, a plant-derived natural product class with a diverse pattern of bioactivity. A withanolide-inspired compound collection was synthesized by making use of three key intermediates that contain this characteristic framework derivatized with different reactive functional groups. Biological evaluation of the compound collection in cell-based assays that monitored biological signal-transduction processes revealed a novel class of Hedgehog signaling inhibitors that target the protein Smoothened. BIOS delivers a collection of compounds with the trans-hydrindane dehydro-δ-lactone scaffold, which are based on the withanolide natural products, in a stereoselective fashion. A biological investigation of the compounds revealed novel and potent inhibitors of the Hedgehog signaling pathway, which bind to the protein Smoothened.

Use of immobilized transition metal complexes as recyclable catalysts for oxidation reactions with hydrogen peroxide as oxidant

A tetradentate Schiff base (teta), obtained from triethylenetetramine and salicylaldehyde, has been covalently bonded to divinylbenzene cross-linked chloromethylated polystyrene. This chelating ligand, abbreviated as PS-teta (PS = polymeric support), reacts with metal chlorides (Cu2+, Co 2+, and Ni2+) in methanol to give polymerbound transition metal complexes, PS-Cu(II)teta/(Cat-1), PS-Ni(II)teta/(Cat-2), and PS-Co(II)teta/(Cat-3), formation of which has been established by various physiochemical methods and spectroscopic techniques. The catalytic potential of these materials has been tested for the oxidation of various alkenes, alkanes, alcohols, and thioethers in the presence of 30% H2O2 as an oxidant. At the same time, these catalysts are very stable and could be reused in oxidation reactions for more than five times without noticeable loss of their catalytic activity. Springer Science+Business Media B.V. 2011.