710324-30-4

Basic information

• Product Name: 2,3-Pentanedione, 4,5-dihydroxy-, (4S)- (9CI)
• Synonyms: 2,3-Pentanedione, 4,5-dihydroxy-, (4S)- (9CI);2,3-Pentanedione,4,5-dihydroxy-, (4S)-;(S)-4,5-Dihydroxy-2,3-pentanedione;(S)-DPD;(4S)-4,5-Dihydroxy-2,3-pentanedione
• CAS NO: 710324-30-4
• Molecular Formula: C₅H₈O₄
• Molecular Weight: 132.11462
• Product Categories: ACETYLGROUP
• Mol File: 710324-30-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 263.0±30.0 °C(Predicted)
• Appearance: /
• Density: 1.311±0.06 g/cm3(Predicted)
• PKA: 11.36±0.20(Predicted)
• CAS DataBase Reference: 2,3-Pentanedione, 4,5-dihydroxy-, (4S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Pentanedione, 4,5-dihydroxy-, (4S)- (9CI)(710324-30-4)
• EPA Substance Registry System: 2,3-Pentanedione, 4,5-dihydroxy-, (4S)- (9CI)(710324-30-4)

Safety Data

• Hazardous Substances Data: 710324-30-4(Hazardous Substances Data)

Usage

General Description

2,3-Pentanedione, 4,5-dihydroxy-, (4S)- (9CI) is a compound with the chemical formula C5H8O3. It is a type of dihydroxyketone, which is a class of organic compounds containing both hydroxyl and carbonyl functional groups. This specific compound exists as a stereoisomer with a chiral center, meaning it has two non-superposable mirror image forms. The (4S)-stereoisomer of 2,3-Pentanedione, 4,5-dihydroxy- has potential applications in the field of pharmaceuticals and chemical synthesis due to its unique structural properties and reactivity. It is important to handle this compound with care due to its potential hazards and safety considerations.

Synthetic route

(S)-4,5-cyclohexylidenedioxy-2,3-pentanedione (848035-01-8) → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
Stage #1: (S)-4,5-cyclohexylidenedioxy-2,3-pentanedione With sulfuric acid-d2 In dimethylsulfoxide-d6; water-d2 for 6h; Stage #2: aq. phosphate buffer;	70%
With sulfuric acid; water-d2 for 2.5h; pH=2; Product distribution / selectivity;
With sulfuric acid; water for 2h; Product distribution / selectivity;

2S-amino-4-[(2S,3R)-2,3,5-trihydroxy-4-oxo-pentanemercaptan]-butyric acid → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
With wild-type S-ribosylhomocysteinase from Bacillus subtilis Enzyme kinetics; Further Variations:; Reagents;

S-ribosyl-L-homocysteine (β-form) → L-homocysteine (6027-13-0) + (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
With MES buffer; E. coli S-ribosylhomocysteinase; S-<(3-carboxy-4-nitrophenyl)thio>-2-aminoethanethiol pH=6; Enzyme kinetics; Kinetics; Further Variations:; Reagents; pH-values; Enzymatic reaction;

1-(2-methoxy-[1,3]-dioxolan-4-yl)-propane-1,2-dione (710324-27-9) → (S)-2,4-Dihydroxy-2-methyl-dihydro-furan-3-one + (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
With phosphate buffer; water; sodium chloride for 36h; pH=6.5;

(S)-bis-O-acetyl-4,5-dihydroxy-2,3-pentanedione → (4S)-5-O-acetyl-4,5-dihydroxy-2,3-pentanedione + (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
With phosphate buffer at 20℃; pH=7.4; Kinetics; Further Variations:; Reagents;

(4S)-5-O-acetyl-4,5-dihydroxy-2,3-pentanedione → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
With phosphate buffer at 20℃; pH=7.4; Kinetics; Further Variations:; Reagents;

2-methoxy-4-(prop-1-ynyl)-[1,3]-dioxolane (710324-26-8) → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 10 percent / potassium permanganate; MgSO4; NaHCO3 / acetone; H2O / 0.33 h / 20 °C 2: H2O; aq. phosphate buffer; NaCl / 36 h / pH 6.5 View Scheme

(R)-pent-3-yne-1,2-diol (500596-40-7) → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 814 mg / sulfuric acid / 1 h / 20 °C 2: 10 percent / potassium permanganate; MgSO4; NaHCO3 / acetone; H2O / 0.33 h / 20 °C 3: H2O; aq. phosphate buffer; NaCl / 36 h / pH 6.5 View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / N,N-dimethyl-formamide / 20 °C 2: sodium periodate; ruthenium(IV) oxide hydrate; water / tetrachloromethane; acetonitrile / 20 °C 3: water / 20 °C / pH 3 View Scheme

(R)-2,2-Dimethyl-4-prop-1-ynyl-[1,3]dioxolane (710324-25-7) → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 81 percent / aq. AcOH / 4 h / 20 °C 2: 814 mg / sulfuric acid / 1 h / 20 °C 3: 10 percent / potassium permanganate; MgSO4; NaHCO3 / acetone; H2O / 0.33 h / 20 °C 4: H2O; aq. phosphate buffer; NaCl / 36 h / pH 6.5 View Scheme

(R)-(-)-1-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-propane-1,2-dione → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
With sulfuric acid In water for 4h;

1-(tert-butyldiphenylsilyloxy)pent-3-yne-2-one (193292-65-8) → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: (-)-(S)-alpine-borane / tetrahydrofuran / 48 h / 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3: sulfuric acid / N,N-dimethyl-formamide / 20 °C 4: sodium periodate; ruthenium(IV) oxide hydrate; water / tetrachloromethane; acetonitrile / 20 °C 5: water / 20 °C / pH 3 View Scheme

(R)-1-(tert-butyldiphenylsilyloxy)pent-3-yn-2-ol (1278444-56-6) → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 2: sulfuric acid / N,N-dimethyl-formamide / 20 °C 3: sodium periodate; ruthenium(IV) oxide hydrate; water / tetrachloromethane; acetonitrile / 20 °C 4: water / 20 °C / pH 3 View Scheme

(R)-1,2-cyclohexylidenedioxypent-3-yne (848035-00-7) → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium periodate; ruthenium(IV) oxide hydrate; water / tetrachloromethane; acetonitrile / 20 °C 2: water / 20 °C / pH 3 View Scheme

1,2-diamino-benzene (95-54-5) + (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4) → (R)-1-(3-methyl-quinoxalin-2-yl)-ethane-1,2-diol

Conditions	Yield
With hydrogenchloride; wild type B. subtilis Co(II)-S-ribosylhomocysteinase In phosphate buffer at 20℃; for 20h; pH=4.5;

(4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4) → phospho-(S)-4,5-dihydroxy-2,3-pentandione (1312297-28-1)

Conditions	Yield
With luxS regulated kinase; ATP; magnesium chloride In water-d2 at 30℃; for 0.166667h; pH=7.2; aq. phosphate buffer;
With LsrK proteins; tris hydrochloride; ATP; sodium chloride; magnesium chloride In water-d2 Enzymatic reaction;

(4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4) → 3-hydroxy-2,4-pentadione-5-phosphate + 3,4,4-trihydroxy-2-pentanone-5-phosphate

Conditions	Yield
Multi-step reaction with 2 steps 1: luxS regulated kinase; ATP; magnesium chloride / water-d2 / 0.17 h / 30 °C / pH 7.2 / aq. phosphate buffer 2: luxS regulated G; diothiothreitol View Scheme

(4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4) → furanosyl borate

Conditions	Yield
With tetrahydroxo borate

Upstream product

• 848035-00-7 (R)-1,2-cyclohexylidenedioxypent-3-yne 
• 1278444-56-6 (R)-1-(tert-butyldiphenylsilyloxy)pent-3-yn-2-ol 
• 193292-65-8 1-(tert-butyldiphenylsilyloxy)pent-3-yne-2-one 
• 848035-01-8 (S)-4,5-cyclohexylidenedioxy-2,3-pentanedione 
• 710324-25-7 (R)-2,2-Dimethyl-4-prop-1-ynyl-[1,3]dioxolane 
• 500596-40-7 (R)-pent-3-yne-1,2-diol 
• 710324-26-8 2-methoxy-4-(prop-1-ynyl)-[1,3]-dioxolane 
• 710324-27-9 1-(2-methoxy-[1,3]-dioxolan-4-yl)-propane-1,2-dione 

Relevant articles and documents

An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing

Autoinducer-2 (AI-2) is a signalling molecule for bacterial inter-species communication. A synthesis of (S)-4,5-dihydroxypentane-2,3-dione (DPD), the precursor of AI-2, is described starting from methyl glycolate. The key step was an asymmetric reduction of a ketone with (S)-Alpine borane. This new method was highly reproducible affording DPD for biological tests without contaminants. The biological activity was tested with the previously available assays and compared with a new method using an Escherichia coli reporter strain thus avoiding the use of the pathogenic Salmonella reporter.

Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer

The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from d-mannitol via (2R)-2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescence-inducing properties in the Vibrio harveyi BB170 strain.

An unexpected switch in the modulation of AI-2-based quorum sensing discovered through synthetic 4,5-dihydroxy-2,3-pentanedione analogues

Quorum sensing (QS) has traditionally referred to a mechanism of communication within a species of bacteria. However, emerging research implicates QS in interspecies communication and competition, and such systems have been proposed in a wide variety of bacteria. The AI-2-based QS system represents the most studied of these proposed interspecies systems, and has been proposed to regulate diverse functions such as bioluminescence, expression of virulence factors, and biofilm formation. As such, the development of modulatory compounds, both agonists and antagonists, is of great interest for the treatment of bacterial infections and the study of unknown AI-2-based QS systems. Toward this end, we have designed and synthesized a panel of 4,5-dihydroxy-2,3-pentanedione/AI-2 analogues and evaluated their effects on the AI-2 QS of various bacteria. The panel of compounds exhibited differential effects in the bacterial cell lines examined, providing a platform for the development of broad-spectrum modulators of AI-2-based QS. Copyright