19790-60-4

Basic information

• Product Name: 3-BENZYLOXY-PROPIONALDEHYDE
• Synonyms: 3-BENZYLOXY-PROPIONALDEHYDE;3-(Phenylmethoxy)propanal;3-Benzyloxypropionaldehyde 96%;3-Benzyloxy-1-propanal;Propanal, 3-(phenylmethoxy)-
• CAS NO: 19790-60-4
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20108
• Mol File: 19790-60-4.mol
• Article Data: 150

Chemical Properties

• Boiling Point: 262.6±15.0 °C(Predicted)
• Flash Point: >110℃
• Appearance: /
• Density: 1.059 g/mL at 25 °C
• Refractive Index: n20/D1.512
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-BENZYLOXY-PROPIONALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BENZYLOXY-PROPIONALDEHYDE(19790-60-4)
• EPA Substance Registry System: 3-BENZYLOXY-PROPIONALDEHYDE(19790-60-4)

Safety Data

• Statements: 52/53
• Safety Statements: 61
• WGK Germany: 3
• Hazardous Substances Data: 19790-60-4(Hazardous Substances Data)

Usage

Description

3-BENZYLOXY-PROPIONALDEHYDE, also known as 3-(Phenylmethoxy)propanal, is an organic compound that serves as an important intermediate in the synthesis of various chemical products. It is characterized by its aldehyde functional group and a benzyloxy substituent, which contribute to its reactivity and utility in chemical reactions.

Uses

Used in Pharmaceutical Industry:
3-BENZYLOXY-PROPIONALDEHYDE is used as a key intermediate for the chemoenzymatic synthesis of threoand erythro-β-hydroxy-L-glutamic acid derivatives. These derivatives are essential components in the development of pharmaceuticals, particularly those targeting various medical conditions and diseases. The compound's role in this synthesis process highlights its importance in the creation of potentially life-saving medications.

Upstream product

• 50-00-0 formaldehyd 
• 6328-48-9 3-benzyloxypropionitrile 
• 4799-68-2 3-benzyloxypropan-1-ol 
• 78314-63-3 3-benzyloxypropionaldehyde diethyl acetal 
• 88191-39-3 (Z)-((hex-3-en-1-yloxy)-methyl)benzene 
• 71998-69-1 (+/-)-4-benzyloxy-butane-1,2-diol 
• 143618-78-4 Oxo-phenyl-acetic acid 3-benzyloxy-propyl ester 
• 107-02-8 acrolein 
• 100-51-6 benzyl alcohol 
• 935-04-6 benzyl vinyl ether 
• 201230-82-2 carbon monoxide 
• 70388-33-9 4-benzyloxybut-1-ene 
• 100-39-0 benzyl bromide 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 87413-14-7 (1S,5R,6R)-6-(2-Benzyloxy-ethyl)-4,5-dimethyl-2,7-dioxa-bicyclo[3.2.0]hept-3-ene 
• 109262-86-4 (3S,4S)-1-(benzyloxy)-4-methylhex-5-en-3-ol 
• 137819-50-2 (3R,4R)-1-(benzyloxy)-4-methylhex-5-en-3-ol 
• 106914-54-9 (3,3-Bis-tert-butylperoxy-propoxymethyl)-benzene 
• 140902-76-7 (E,5RS)-7-benzyloxy-1-chloro-5-hydroxyhepten-3-one 
• 119405-98-0 1,1-Dibromo-4-(phenylmethoxy)-1-butene 
• 116376-13-7 (4R^*,3R^*)-1-(benzyloxy)-4-methoxy-5-hexen-3-ol 
• 128217-53-8 5-benzyloxy-2(E)-pentenoic acid methyl ester 
• 94807-44-0 1-acetyl-3-(3-benzyloxypropylidene)-2,5-piperazinedione 
• 105346-31-4 5-(2-benzyloxyethyl)-3-hydroxy-4-phenyl-2(5H)-furanone 
• 123268-67-7 ((E)-3-Benzyloxy-propenyloxy)-tert-butyl-dimethyl-silane 
• 111322-01-1 (R)-1-benzyloxy-hex-5-en-3-ol 
• 91285-62-0 (S)-1-(benzyloxy)-3-hydroxyhex-5-ene 
• 119046-50-3 (E)-5-Benzyloxy-1-trimethylsilanyl-pent-1-en-3-ol 

Relevant articles and documents

Chiral polypropionate subunit by a chemoenzymatic approach

Enzymatic desymmetrization of meso-4-methyl-3,5-syn-dioxolan- 1,3,5,7- tetrol was found to be highly enantioselective leading to both acetylated enantiomers with high enantiomeric excess.

Asymmetric synthesis of D- and L-2-deoxy-4-thioriboses

Both D- and L-enantiomers of 2-deoxy-4-thioribose derivatives 12 and 17 were prepared stereospecifically in 12 steps from 1,3-propanediol. The key intermediary 2,3-epoxy alcohols, 8 and 15 were obtained with high enantiomeric excess by the Sharpless asymmetric epoxidation using (+)-L- diethyl tartrate and (-)-D-diethyl tartrate.

Gold-Catalyzed Formal Hexadehydro-Diels-Alder/Carboalkoxylation Reaction Cascades

A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.

Pyrazole Agonist of the Apelin Receptor Improves Symptoms of Metabolic Syndrome in Mice

Apelin receptor agonism improves symptoms of metabolic syndrome. However, endogenous apelin peptides have short half-lives, making their utility as potential drugs limited. Previously, we had identified a novel pyrazole-based agonist scaffold. Systematic modification of this scaffold was performed to produce compounds with improved ADME properties. Compound 13 with favorable agonist potency (cAMPi EC50 = 162 nM), human liver microsome stability (T1/2 = 62 min), and pharmacokinetic profile in rodents was identified. The compound was tested in a mouse model of diet-induced obesity (DIO) and metabolic syndrome for efficacy. Treatment with 13 led to significant weight loss, hypophagia, improved glucose utilization, reduced liver steatosis, and improvement of disease-associated biomarkers. In conclusion, a small-molecule agonist of the apelin receptor has been identified that is suitable for in vivo investigation of the apelinergic system in DIO and perhaps other diseases where this receptor has been implicated to play a role.