39590-81-3

Basic information

• Product Name: 1,1-Bis(hydroxymethyl)cyclopropane
• Synonyms: CYCLOPROPYLIDENEDIMETHANOL;CYCLOPROPANE DIMETHANOL;1,1-BIS(HYDROXYMETHYL)CYCLOPROPANE;1,1-CYCLOPROPANEDIMETHANOL;1,1-DIMETHYLCYCLOPROPANE;(1-HYDROXYMETHYLCYCLOPROPYL)METHANOL;1,1-Cyclopropane dimethanlol;1,1-Cyclopropyldimethanol
• CAS NO: 39590-81-3
• Molecular Formula: C5H10O2
• Molecular Weight: 102.13
• Product Categories: Propanes/propenes;Hydroxymethyl's;Alkohols;API intermediates;Ring Systems;Thiophenes
• Mol File: 39590-81-3.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 235-236 °C(lit.)
• Flash Point: >230 °F
• Appearance: Liquid
• Density: 1.065 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00601mmHg at 25°C
• Refractive Index: n20/D 1.4700(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Ethyl Acetate (Slightly)
• PKA: 14.80±0.10(Predicted)
• CAS DataBase Reference: 1,1-Bis(hydroxymethyl)cyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Bis(hydroxymethyl)cyclopropane(39590-81-3)
• EPA Substance Registry System: 1,1-Bis(hydroxymethyl)cyclopropane(39590-81-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 39590-81-3(Hazardous Substances Data)

Usage

Description

1,1-Bis(hydroxymethyl)cyclopropane, also known as Glycerol, is a colorless to yellow liquid with a sweet taste and odor. It is a simple polyol compound that is widely used in various industries due to its unique properties.

Uses

1,1-Bis(hydroxymethyl)cyclopropane is used as a synthetic intermediate for the production of morphine alkaloids, which are important pharmaceutical compounds with potent analgesic and sedative effects. It is also utilized as an inhibitor of 5-lipoxygenase, an enzyme involved in the production of leukotrienes, which are inflammatory mediators. By inhibiting this enzyme, 1,1-Bis(hydroxymethyl)cyclopropane can potentially be used in the treatment of various inflammatory conditions.
Used in Pharmaceutical Industry:
1,1-Bis(hydroxymethyl)cyclopropane is used as a synthetic intermediate for the production of morphine alkaloids, which are essential in the development of potent analgesic and sedative medications. Its role in the synthesis of these alkaloids makes it a valuable component in the pharmaceutical industry.
Used in Enzyme Inhibition:
1,1-Bis(hydroxymethyl)cyclopropane is used as an inhibitor of 5-lipoxygenase, an enzyme that plays a crucial role in the synthesis of leukotrienes, which are involved in inflammatory processes. By inhibiting this enzyme, it can potentially be employed in the development of treatments for various inflammatory conditions, making it a valuable compound in the field of enzyme inhibition and inflammation management.

InChI:InChI=1/C5H10O2/c6-3-5(4-7)1-2-5/h6-7H,1-4H2

Upstream product

• 1559-02-0 diethyl cyclopropane-1,1-dicarboxylate 
• 148420-14-8 1,1-cyclopropanedimethanol diacetate 
• 598-10-7 cyclopropane-1,1-dicarboxylic acid 
• 1120-56-5 methylidenecyclobutane 
• 55754-69-3 [1-(chloromethyl)cyclopropyl]methanol 
• 6914-71-2 dimethyl 1,1-cyclopropanedicarboxylate 
• 7732-18-5 water 
• 304-59-6 Rochelle's salt 

Downstream Products

• 29086-41-7 1,1-bis(bromomethyl)cyclopropane 
• 101595-74-8 1,1-bis-benzenesulfonyloxymethyl-cyclopropane 
• 49640-66-6 1‐(hydroxymethyl)cyclopropane‐1‐carboxylic acid 
• 22308-08-3 cyclopropane-1,1-diyldimethanediyl bis(4-methylbenzenesulfonate) 
• 89729-09-9 5,7-dioxa-6-thia-spiro[2.5]octane 6-oxide 
• 83321-23-7 1,1-bis(iodomethyl)cyclopropane 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 148420-14-8 1,1-cyclopropanedimethanol diacetate 
• 136476-38-5 cyclopropane-1,1-diylbis(methylene) dimethanesulfonate 
• 152922-71-9 1-(hydroxymethyl)cyclopropaneacetonitrile 
• 598-10-7 cyclopropane-1,1-dicarboxylic acid 
• 177200-76-9 {1-[(benzyloxy)methyl]cyclopropyl}methanol 
• 208642-96-0 2-methanesulfonyl-benzenesulfonic acid 3-(1-hydroxymethyl-cyclopropylmethoxy)-5-methyl-phenyl ester 
• 208642-98-2 N-{1-[[5-methyl-3-(2-methylsulfonylphenylsulfonyloxy)phenoxy]methyl]cyclopropylmethoxy}amine 

Relevant articles and documents

Cyclopropyloxetanes. Reactions of 5-Oxaspirohexane with Hydrogen Halides

The title cyclopropyloxetane reacted with aqueous hydrogen chloride, bromide, and iodide to give mixtures of the corresponding 1-(halogenomethyl)-1-(hydroxymethyl)cyclopropane and 1-halogeno-1-(hydroxymethyl)cyclobutane.Keywords: Bicyclobutonium ion; Cyclopropyl carbinyl cation; Molecular rearrangement; Oxetane.

Structure-activity relationship study of β-oxidation resistant indole-based 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) receptor antagonists

5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is formed from 5S-hydroxy-6,8,11,14-eicosatetraenoic acid (5-HETE) by the 5-lipoxygenase (5-LO) pathway under conditions associated with oxidative stress. 5-Oxo-ETE is an important pro-inflammatory mediator, which stimulates the migration of eosinophils via a selective G-protein coupled receptor, known as the OXE receptor (OXE-R). Previously, we designed and synthesized structural mimics of 5-oxo-ETE such as 1 using an indole scaffold. In the present work, we added various substituents at C-3 of this moiety to block potential β-oxidation of the 5-oxo-valerate side chain, and investigated the structure-activity relationships of the resulting novel β-oxidation-resistant antagonists. Cyclopropyl and cyclobutyl substituents were well tolerated in this position, but were less potent as the highly active 3S-methyl compound. It seems likely that 3-alkyl substituents can affect the conformation of the 5-oxovalerate side chain containing the critical keto and carboxyl groups, thereby affecting interaction with the OXE-receptor.

Substituted 4-morpholine N-arylsulfonamides as γ-secretase inhibitors

The design, synthesis, SAR, and biological profile of a substituted 4-morpholine sulfonamide series of γ-secretase inhibitors (GSIs) were described. In several cases, the resulting series of GSIs reduced CYP liabilities and improved γ-secretase inhibition activity compared to our previous research series. Selected compounds demonstrated significant reduction of amyloid-β (Aβ) after acute oral dosing in a transgenic animal model of Alzheimer's disease (AD).