24923-77-1

Basic information

• Product Name: (4S)-4-hydroxy-3-methylidenedihydrofuran-2(3H)-one
• Synonyms: 2(3H)-Furanone, dihydro-4-hydroxy-3-methylene-, (S)-
• CAS NO: 24923-77-1
• Molecular Formula: C₅H₆O₃
• Molecular Weight: 114.0993
• Mol File: 24923-77-1.mol

Chemical Properties

• Boiling Point: 328.8°C at 760 mmHg
• Flash Point: 163.5°C
• Density: 1.27g/cm³
• Vapor Pressure: 1.38E-05mmHg at 25°C
• Refractive Index: 1.494
• CAS DataBase Reference: (4S)-4-hydroxy-3-methylidenedihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4-hydroxy-3-methylidenedihydrofuran-2(3H)-one(24923-77-1)
• EPA Substance Registry System: (4S)-4-hydroxy-3-methylidenedihydrofuran-2(3H)-one(24923-77-1)

Safety Data

• Hazardous Substances Data: 24923-77-1(Hazardous Substances Data)

Upstream product

• 123172-67-8 C₁₉H₁₆O₃ 
• 917506-89-9 methyl 4-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylenebutyrate 
• 796989-44-1 2-bromo-1-butene-3,4-diol 
• 73945-76-3 (S)-2-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)propenic acid 
• 73945-71-8 (+)-Methyl β,γ-dihydroxy-α-methylenebutyrate 
• 74006-38-5 2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-acrylic acid 
• 101198-77-0 3-Benzenesulfinyl-4-hydroxy-3-methyl-dihydro-furan-2-one 
• 24923-78-2 α-Methylen-β,γ-dihydroxy-buttersaeure 
• 547-65-9 α-methylene-γ-butyrolactone 
• 73945-75-2 Benzoic acid 2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyl ester 
• 73945-74-1 (+)-(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol 
• 883988-87-2 (S)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propenal 
• 189351-43-7 2(R),6(S)-2,6-di-(acetoxymethyl)-5-methylene-1,3-dioxan-4-one 
• 123434-22-0 (S) methyl 4-acetoxy-3-hydroxy-2-methylenebutanoate 

Relevant articles and documents

Purification and characterization of a tuliposide-converting enzyme from bulbs of tulipa gesneriana

An enzyme that catalyzes the stoichiometric conversion of 6-tuliposide into tulipalin was purified and characterized from bulbs of Tulipa gesneriana. The enzyme appeared to be a dimer, the relative molecular mass (Mr) of each subunit being 34,900; it had maximum activity and stability at neutral pH and moderate temperature. The enzyme preferentially acted on such glucose esters as 6-tuliposides, and to a lesser extent on /7-nitrophenylacetate.

First total synthesis of 6-tuliposide B

Labile (+)-6-tuliposide B, an antimicrobial compound produced by tulip, was synthesized in nine steps from d-glucose via the Baylis-Hillman reaction of 2-(tert-butyldimethylsilyloxy)-acetaldehyde with 6-O-acryloyl-1-O-(2-trimethylsilylethyl)-β-d-glucopyranoside, followed by a mild deprotection procedure using TFA in CH2Cl2.

A facile method for the preparation of α-methylene-γ-butyrolactones from tulip tissues by enzyme-mediated conversion

We developed a facile method of enzyme-mediated conversion of 6-tuliposide to α-methylene-γ-butyrolactone (tulipalin). We used a tuliposide-converting enzyme for the conversion of 6-tuliposides extracted from tulip tissues into the corresponding tulipalins in high yields within 2 h at pH 7.0. The resulting tulipalins were selectively extracted by using several organic solvents.

A NEW TEMPLATE of MITSUNOBU ACYLATE CLEAVABLE in NONALKALINE CONDITIONS

The Mitsunobu inversion is one of the reliable methods for stereospecific substitution of chiral alcohols, but its deacylation step has limited the substrate scope. Here, we propose a new template of the Mitsunobu acylate that can be deacylated in non-alkaline treatments. The 3,4-dihydroxy-2-methylenebutanoate was selected as a template structure, and its acetonide- or bisTBS derivatives were synthesized. The latter especially showed excellent inversion efficiency (up to >99% ee) and good elimination performance for a series of secondary alcohols in near-neutral conditions. The results demonstrated the applicability of the new template for the substrates labile in alkaline conditions, such as a-hydroxyesters.

Substrate specificity of tuliposide-converting enzyme, a unique non-ester-hydrolyzing carboxylesterase in tulip: Effects of the alcohol moiety of substrate on the enzyme activity

6-Tuliposides A (PosA) and B (PosB) are glucose esters accumulated in tulip (Tulipa gesneriana) as major defensive secondary metabolites. Pos-converting enzymes (TgTCEs), which we discovered previously from tulip, catalyze the conversion reactions of PosA

Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA

The enzyme MurA performs an essential step in peptidoglycan biosynthesis and is therefore a target for the discovery of novel antibacterial compounds. We report here the inhibition of MurA by natural products from tulips (tulipalines and tuliposides), and the structure-activity relationships of various derivatives. The inhibition of MurA can be related to antibacterial activity, and MurA is probably one of the relevant molecular targets of the tulipaline derivatives. MurA inhibition by this class of compounds depends on the presence of the substrate UNAG, which indicates non-covalent suicide inhibition as observed previously for cnicin. With respect to selectivity, however, the reactivity against arbitrary sulfhydryl groups, such as in glutathione, could not yet be sufficiently separated from MurA inhibition in the present dataset.

Synthesis of tulipalin B and 1-O-methyl-6-tuliposide B

Toward the total synthesis of 6-tuliposide B, facile synthesis of tulipalin B and 1-O-methyl-6-tuliposide B (Methyl 6-0-((S)-3′,4′-dihydroxy-2′-methylenebutanoyl)-β-D-glucopyranoside) has been achieved.

Synthesis of (-)-tuliparin B utilizing 2-bromo-1-alkenes conveniently synthesized from the 3-0-substituted 1,2-dibromoalkane system by regioselective elimination

Synthesis of (-)-tulipalin B with a variety of biological properties including cutaneous allergenic activity, was accomplished by using the 2-bromo-1-alkenes synthesized by the regioselective HBr elimination reaction of 3-acyloxy-1,2-dibromoalkanes.

The asymmetric Baylis-Hillman reaction as a template in organic synthesis

The Bayils-Hillman reaction of camphor-based acrylates has been demonstrated to result in the formation of products with high optical purity. A model that explains these results and the use of these products in the formation of anti aldol adducts is discu