186393-31-7

Basic information

• Product Name: trans-3,4-Dihydroxypyrrolidine
• Synonyms: trans-3,4-Dihydroxypyrrolidine;trans-3,4-pyrrolidinediol(SALTDATA: FREE);(3R,4R)-3,4-Pyrrolidinediol;3,4-Pyrrolidinediol,(3R,4R)-
• CAS NO: 186393-31-7
• Molecular Formula: C₄H₉NO₂
• Molecular Weight: 103.12
• Product Categories: pharmacetical
• Mol File: 186393-31-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 98-99 °C
• Boiling Point: 232.305 °C at 760 mmHg
• Flash Point: 144.006 °C
• Appearance: /
• Density: 1.309 g/cm³
• Vapor Pressure: 0.011mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: 2-8°C(protect from light)
• PKA: 14.08±0.40(Predicted)
• CAS DataBase Reference: trans-3,4-Dihydroxypyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3,4-Dihydroxypyrrolidine(186393-31-7)
• EPA Substance Registry System: trans-3,4-Dihydroxypyrrolidine(186393-31-7)

Safety Data

• Hazardous Substances Data: 186393-31-7(Hazardous Substances Data)

Usage

General Description

Trans-3,4-dihydroxypyrrolidine is a chemical compound with the molecular formula C4H9NO2. It is a pyrrolidine derivative with two hydroxyl groups attached to the third and fourth carbon atoms in the trans configuration. trans-3,4-Dihydroxypyrrolidine is a chiral molecule, meaning it has a non-superimposable mirror image. It has been found to have potential pharmacological activities, including anticonvulsant and anti-inflammatory properties. Additionally, it has been studied for its potential use as a chiral building block in organic synthesis. However, further research is needed to fully understand the potential uses and effects of trans-3,4-dihydroxypyrrolidine.

InChI:InChI=1/C4H9NO2/c6-3-1-5-2-4(3)7/h3-7H,1-2H2/t3-,4-/m1/s1

Upstream product

• 163439-82-5 (3R,4R)-1-benzyl-3,4-pyrrolidinediol 
• 163439-83-6 (+)-(3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxypyrrolidine 
• 943243-01-4 1,4-(hydroxyimino)-2,3-di-O-(methoxymethyl)-1,4-dideoxy-D-threitol 

Downstream Products

• 1255303-59-3 {4-[2-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)ethoxy]pyridin-2-yl}-{3-[4-(4-ethylbenzyloxy)-3-methoxyphenyl]azetidin-1-yl}methanone 
• 1414873-40-7 C₄₄H₇₁N₄O₁₁P 

Relevant articles and documents

Synthesis and evaluation of amino-threoses in d- and l-series: Are five membered ring amino-sugars more potent glycosidase inhibitors than the six membered ones?

Cyclic d- and l-4-aminothreose were synthesised from ethyl d- and l-tartrate, respectively. d-Aminothreose was a potent inhibitor of α-glucosidase and of α-mannosidase. From the glycosidase inhibition potencies of the four 4-amino-4-deoxy-tetroses, the contribution of binding of each functionality of the 5 and 6 membered ring amino-sugars towards the various glycosidases is discussed.

3-Hydroxypyrrolidine and (3,4)-dihydroxypyrrolidine derivatives: Inhibition of rat intestinal α-glucosidase

Thirteen pyrrolidine-based iminosugar derivatives have been synthesized and evaluated for inhibition of α-glucosidase from rat intestine. The compounds studied were the non-hydroxy, mono-hydroxy and dihydroxypyrrolidines. All the compounds were N-benzylated apart from one. Four of the compounds had a carbonyl group in the 2,5-position of the pyrrolidine ring. The most promising iminosugar was the trans-3,4-dihydroxypyrrolidine 5 giving an IC50 of 2.97 ± 0.046 and a KI of 1.18 mM. Kinetic studies showed that the inhibition was of the mixed type, but predominantly competitive for all the compounds tested. Toxicological assay results showed that the compounds have low toxicity. Docking studies showed that all the compounds occupy the same region as the DNJ inhibitor on the enzyme binding site with the most active compounds establishing similar interactions with key residues. Our studies suggest that a rotation of ～90° of some compounds inside the binding pocket is responsible for the complete loss of inhibitory activity. Despite the fact that activity was found only in the mM range, these compounds have served as simple molecular tools for probing the structural features of the enzyme, so that inhibition can be improved in further studies.

Exocyclic deoxyadenosine adducts of 1,2,3,4-diepoxybutane: Synthesis, structural elucidation, and mechanistic studies

1,2,3,4-Diepoxybutane (DEB) is considered the ultimate carcinogenic metabolite of 1,3-butadiene, an important industrial chemical and environmental pollutant present in urban air. Although it preferentially modifies guanine within DNA, DEB induces a large number of A → T transversions, suggesting that it forms strongly mispairing lesions at adenine nucleobases. We now report the discovery of three potentially mispairing exocyclic adenine lesions of DEB: N6,N6-(2,3-dihydroxybutan-1,4-diyl)-2′- deoxyadenosine (compound 2), 1,N6-(2-hydroxy-3-hydroxymethylpropan-1, 3-diyl) -2′-deoxyadenosine (compound 3), and 1,N6-(1- hydroxymethyl-2-hydroxypropan-1,3-diyl)-2′-deoxyadenosine (compound 4). The structures and stereochemistry of the novel DEB-dA adducts were determined by a combination of UV and NMR spectroscopy, tandem mass spectrometry, and independent synthesis. We found that synthetic N6-(2-hydroxy-3,4- epoxybut-1-yl)-2′-deoxyadenosine (compound 1) representing the product of N6-adenine alkylation by DEB spontaneously cyclizes to form 3 under aqueous conditions or 2 under anhydrous conditions in the presence of an organic base. Compound 3 can be interconverted with 4 by a reversible unimolecular pericyclic reaction favoring 4 as a more thermodynamically stable product. Both 3 and 4 are present in double stranded DNA treated with DEB in vitro and in liver DNA of laboratory mice exposed to 1,3-butadiene by inhalation. We propose that in DNA under physiological conditions, DEB alkylates the N-1 position of adenine in DNA to form N1-(2-hydroxy-3,4-epoxybut-1-yl)-adenine adducts, which undergo an SN2-type intramolecular nucleophilic substitution and rearrangement to give 3 (minor) and 4 (major). Formation of exocyclic DEB-adenine lesions following exposure to 1,3-butadiene provides a possible mechanism of mutagenesis at the A:T base pairs.