470-29-1

Basic information

• Product Name: 2,4-DIHYDROXY-3,3-DIMETHYLBUTANOIC ACID
• Synonyms: 2,4-DIHYDROXY-3,3-DIMETHYLBUTANOIC ACID;pantoic acid;Butanoic acid,2,4-dihydroxy-3,3-diMethyl-
• CAS NO: 470-29-1
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.16
• Mol File: 470-29-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 124 °C
• Boiling Point: 368.7°Cat760mmHg
• Flash Point: 191°C
• Appearance: /
• Density: 1.259g/cm³
• Vapor Pressure: 6.16E-07mmHg at 25°C
• Refractive Index: 1.496
• PKA: 3.73±0.27(Predicted)
• CAS DataBase Reference: 2,4-DIHYDROXY-3,3-DIMETHYLBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIHYDROXY-3,3-DIMETHYLBUTANOIC ACID(470-29-1)
• EPA Substance Registry System: 2,4-DIHYDROXY-3,3-DIMETHYLBUTANOIC ACID(470-29-1)

Safety Data

• Hazardous Substances Data: 470-29-1(Hazardous Substances Data)

Usage

General Description

2,4-Dihydroxy-3,3-dimethylbutanoic acid, also known as homogentisic acid, is a chemical compound that is a precursor to the formation of the pigment melanin. It is found naturally in the body as an intermediate in the metabolism of the amino acids phenylalanine and tyrosine. Elevated levels of homogentisic acid can be associated with a rare genetic disorder called alkaptonuria, which causes a buildup of the compound in the connective tissues, leading to dark pigmentation and arthritis. 2,4-Dihydroxy-3,3-dimethylbutanoic acid is also used in the synthesis of pharmaceuticals and as a reagent in organic chemistry.

InChI:InChI=1/C6H12O4/c1-6(2,3-7)4(8)5(9)10/h4,7-8H,3H2,1-2H3,(H,9,10)/t4-/m0/s1

Synthetic route

DL-pantolactone → D-(-)-pantolactone + (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
With sodium hydroxide In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water	A 82% B n/a

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + hydrogen cyanide (74-90-8) → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
das α-Oxy-β.β-dimethyl-butyrolaceton entsteht durch Verseifung des entstandenen Oxynitrils mit Salzsaeure;

α-oxy-β.β-dimethyl-butyrolactone → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
With -base Die Salze entstehen;

DL-α-hydroxy-β.β-dimethyl-γ-butyrolactone → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
With sodium hydroxide das Natriumsalz entsteht;
With barium dihydroxide das Bariumsalz entsteht;

hydrogen cyanide (74-90-8) + sodium bisulfite- compound of β-oxy-α,α-dimethyl-propionaldehyde → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
das α-Oxy-β.β-dimethyl-butyrolaceton entsteht durch Verseifung des entstandenen Oxynitrils mit Salzsaeure;

pantolactone (79-50-5) → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
With water; sodium hydroxide In water at 30℃; pH=6.7 - 6.9; Enzymatic reaction;

isobutyraldehyde (78-84-2) + Glyoxilic acid (298-12-4) → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
Stage #1: isobutyraldehyde; Glyoxilic acid With triethylamine at 20 - 30℃; for 3h; Stage #2: With 5%-palladium/activated carbon; hydrogen In 1,2-dichloro-ethane at 20 - 25℃; for 4h; Reagent/catalyst; Temperature; Solvent; Autoclave;

2,4-dihydroxy-3,3-dimethylbutanoic acid ethyl ester → (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1)

Conditions	Yield
Stage #1: 2,4-dihydroxy-3,3-dimethylbutanoic acid ethyl ester With water; sodium hydroxide at 100℃; for 1h; Green chemistry; Stage #2: With hydrogenchloride In water pH=3 - 4; Temperature; Green chemistry;	8.1 g

(+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1) → pantolactone (79-50-5)

Conditions	Yield
With sulfuric acid at 80 - 85℃; for 3h; Temperature;	98.3%

3-aminobutanoic acid ethyl ester (5303-65-1) + (+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1) → (+/-)-3-pantoylamino-butyric acid

(+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1) → L-pantoic acid (1112-32-9)

Conditions	Yield
With water; Quinine das Chininsalz entsteht;

(+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1) → D-pantoic acid (1112-33-0)

Conditions	Yield
With water; Quinine durch optische Spaltung;
With ethanol; Quinine durch optische Spaltung;
With pyridine; water; Quinine durch optische Spaltung;

Upstream product

• 597-31-9 2,2-dimethyl-3-hydroxypropionaldehyde 
• 74-90-8 hydrogen cyanide 
• 78-84-2 isobutyraldehyde 
• 298-12-4 Glyoxilic acid 
• 79-50-5 pantolactone 

Downstream Products

• 1112-32-9 L-pantoic acid 
• 79-50-5 pantolactone 

Relevant articles and documents

Synthetic method of 2, 4-dihydroxyl-3, 3-dimethyl butyric acid

The invention discloses a synthetic method of 2, 4-dihydroxyl-3, 3-dimethyl butyric acid. The synthetic method of 2, 4-dihydroxyl-3, 3-dimethyl butyric acid comprises following steps: 1), isobutyraldehyde and ethyl oxalyl monochloride are subjected to aldol condensation under the effect of RM to generate 3, 3-dimethyl-2, 4-dioxo ethyl butyrate, wherein M is used for representing an alkali metal, and R is used for representing alkyloxy, hydrogen, amino, or alkyl; 2), 3, 3-dimethyl-2, 4-dioxo ethyl butyrate is subjected to reduction reaction to generate 2, 4-dihydroxyl-3, 3-dimethyl ethyl butyrate, and 2, 4-dihydroxyl-3, 3-dimethyl ethyl butyrate is subjected to hydrolysis so as to obtain a target product. According to the synthetic method, isobutyraldehyde and ethyl oxalyl monochloride are adopted as initial raw materials, aldol condensation reaction, reduction reaction, and hydrolysis reaction are adopted to obtain the target product, compared with the prior art, the advantages of the synthetic method are that: no hypertoxic raw material is adopted, operation safety is high, reaction conditions are not server, and operation is simple, and is convenient to control.

A new chemo-enzymatic route to chiral 2-hydroxy-4-phenylbutyrates by combining lactonase-mediated resolution with hydrogenation over Pd/C

A new chemo-enzymatic route to both isomers of 2-hydroxy-4-phenylbutyric acid is reported. The key step is the lactonase-catalyzed hydrolysis of cis- and trans-2-hydroxy-4-phenyl-4-butyrolactones followed by hydrogenation over Pd/C to afford optically pure 2-hydroxy-4-phenylbutyric acid.