306-23-0

Basic information

• Product Name: 3-(4-Hydroxyphenyl)lactate
• Synonyms: 3-[4-HYDROXYPHENYL]-2-HYDROXYPROPANOIC ACID;2-HYDROXY-3-(4-HYDROXYPHENYL)PROPANOIC ACID;2-HYDROXY-3-(P-HYDROXYPHENYL)PROPIONIC ACID;BETA ,4-DIHYDROXYBENZENEPROPANOIC ACID;A-(P-HYDROXYPHENYL)-DL-LACTIC ACID;DL-P-HYDROXYPHENYLLACTIC ACID;DL-4-HYDROXYPHENYLLACTIC ACID;PARA-HYDROXYPHENYLLACTICACID
• CAS NO: 306-23-0
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 181.17
• Mol File: 306-23-0.mol

Chemical Properties

• Melting Point: 140 °C(Solv: water (7732-18-5))
• Boiling Point: 275.56°C (rough estimate)
• Flash Point: 218.6 °C
• Appearance: /
• Density: 1.2481 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4345 (estimate)
• PKA: 3.80±0.10(Predicted)
• CAS DataBase Reference: 3-(4-Hydroxyphenyl)lactate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-Hydroxyphenyl)lactate(306-23-0)
• EPA Substance Registry System: 3-(4-Hydroxyphenyl)lactate(306-23-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 306-23-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Nutraceutical Applications:
3-(4-Hydroxyphenyl)lactate is used as a precursor in the synthesis of rosmarinic acid, which has significant pharmaceutical and nutraceutical applications. Rosmarinic acid is known for its various health benefits, including anti-inflammatory, antioxidant, and antimicrobial properties.
Used in Antifungal Applications:
3-(4-Hydroxyphenyl)lactate exhibits antifungal activity, making it a valuable compound for the development of new antifungal agents. This property can be utilized in the agricultural and medical industries to combat fungal infections and protect crops from fungal diseases.
Used in Chemical Synthesis:
3-(4-Hydroxyphenyl)lactate is used as a reagent in the synthesis of 2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactic acid, an important intermediate in the biosynthesis of rosmarinic acid. This application highlights its importance in the chemical industry for the production of valuable compounds with diverse applications.

InChI:InChI=1/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)/p-1

Upstream product

• 156-39-8 4-hydroxyphenylpiruvic acid 
• 2922-41-0 (p-aminophenyl)alanine 
• 52178-61-7 2-hydroxy-3-(4-hydroxyphenyl)acrylic acid 
• 51095-47-7 methyl 3-(4-hydroxyphenyl)-2-hydroxypropionate 
• 52507-17-2 (Z)-4-((2-methyl-5-oxooxazol-4(5H)-ylidene)methyl)phenyl acetate 
• 556-02-5 ?Tyr 
• 7782-77-6 cis-nitrous acid 
• 15220-05-0 (+/-)-2-hydroxy-3-(4-hydroxy-3,5-diiodo-phenyl)-propionic acid 
• 154722-74-4 methyl 2-oxo-3-(4-hydroxyphenyl)propionate 
• 64896-33-9 (Z)-2-acetamido-3-(p-hydroxyphenyl)-2-propenic acid 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 15220-05-0 (+/-)-2-hydroxy-3-(4-hydroxy-3,5-diiodo-phenyl)-propionic acid 
• 35772-94-2 (+/-)-2-hydroxy-3-(4-hydroxy-3,5-dinitro-phenyl)-propionic acid 
• 99358-35-7 2-hydroxy-3-(4-hydroxy-3-nitro-phenyl)-propionic acid 
• 51095-47-7 methyl 3-(4-hydroxyphenyl)-2-hydroxypropionate 
• 395098-94-9 (+/-)-tert-butyl 3-(4-hydroxyphenyl)lactate 
• 395098-95-0 (+/-)-tert-butyl 3-(4-tert-butyldimethylsilyloxyphenyl)lactate 
• 395098-97-2 (+/-)-tert-butyl 2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactate 
• 395098-96-1 (+/-)-tert-butyl 2-O-(4-tert-butyldimethylsilylcoumaroyl)-3-(4-tert-butyldimethylsilyloxyphenyl)lactate 
• 299175-87-4 4-(5,5-dimethyl-2-oxodioxolan-3-ylmethyl)phenol 
• 7339-87-9 4-hydroxyphenylacetaldehyde 
• 1410789-22-8 3-(m-chloro-m-bromo-p-hydroxyphenyl)-D,L-lactic acid 
• 1350441-12-1 3-(4-t-butoxycarbonylmethoxyphenyl)-2-(4-chlorobenzyloxy)propionic acid methyl ester 
• 1350441-13-2 3-(4-carboxymethoxyphenyl)-2-(4-chlorobenzyloxy)propionic acid methyl ester 
• 1350441-56-3 3-(4-t-butoxycarbonylmethoxyphenyl)-2-(3-chlorobenzyloxy)propionic acid methyl ester 

Relevant articles and documents

A Phenylpyruvic Acid Reductase Is Required for Biosynthesis of Tropane Alkaloids

Solanaceous medicinal plants produce tropane alkaloids (TAs). We discovered a novel gene from Atropa belladonna, AbPPAR, which encodes a phenylpyruvic acid reductase required for TA biosynthesis. AbPPAR was specifically expressed in root pericycles and endodermis. AbPPAR was shown to catalyze reduction of phenylpyruvic acid to phenyllactic acid, a precursor of TAs. Suppression of AbPPAR disrupted TA biosynthesis through reduction of phenyllactic acid levels. In summary, we identified a novel enzyme involved in TA biosynthesis.

Mechanistic study of the radical SAM-dependent amine dehydrogenation reactions

The radical SAM enzyme NosL catalyzes the conversion of l-Trp to 3-methyl-2-indolic acid, and this reaction is initiated by the 5′-deoxyadenosyl (dAdo) radical-mediated hydrogen abstraction from the l-Trp amino group. We demonstrate here that when d-Trp was used in the NosL reaction, hydrogen abstraction occurs promiscuously at both the amino group and Cα of d-Trp. These results inspired us to establish the detailed mechanism of l-Trp amine dehydrogenation catalyzed by a NosL mutant, and to engineer a novel radical SAM-dependent l-Tyr amine dehydrogenase from the thiamine biosynthesis enzyme ThiH.

Latifolicinin A from a Fermented Soymilk Product and the Structure-Activity Relationship of Synthetic Analogues as Inhibitors of Breast Cancer Cell Growth

The functional components in soymilk may vary depending upon the fermentation process. A fermented soymilk product (FSP) obtained by incubation with the microorganisms of intestinal microflora was found to reduce the risk of breast cancer. Guided by the inhibitory activities against breast cancer cells, two cytotoxic compounds, daidzein and (S)-latifolicinin A, were isolated from the FSP by repetitive extraction and chromatography. Latifolicinin A is the n-butyl ester of β-(4-hydroxyphenyl)lactic acid (HPLA). A series of the ester and amide derivatives of (S)-HPLA and l-tyrosine were synthesized for evaluation of their cytotoxic activities. In comparison, (S)-HPLA derivatives exhibited equal or superior inhibitory activities to their l-tyrosine counterparts, and (S)-HPLA amides showed better cytotoxic activities than their corresponding esters. In particular, (S)-HPLA farnesyl amide was active to triple-negative MDA-MB-231 breast cancer cells (IC50 = 27 μM) and 10-fold less toxic to Detroit-551 normal cells.

METHOD FOR SYNTHESIS OF KETO ACID OR AMINO ACID BY HYDRATION OF ACETHYLENE COMPOUND

An object of the present invention is to provide a method for synthesis of keto acids by hydration of an acetylene compound (acetylene-carboxylic acids) under mild conditions free from harmful mercury catalysts and a method for synthesis of amino acids from acetylene-carboxylic acids in a single container (one-pot or tandem synthesis). In one embodiment of the method according to the present invention for synthesis of keto acids, acetylene-carboxylic acids is hydrated in the presence of a metal salt represented by General Formula (1), where M1 represents an element in Group VIII, IX, or X of the periodic table, and X1, X2, or X3 ligand represents halogen, H2O, or a solvent molecule, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k × m = L × n.

pH-Dependent Chemoselective Synthesis of α-Amino Acids. Reductive Amination of α-Keto Acids with Ammonia Catalyzed by Acid-Stable Iridium Hydride Complexes in Water

An acid-stable hydride complex [Cp*IrIII(bpy)H]+ {1, Cp* = η5-C5Me5, bpy = 2,2′-bipyridine} serves as the active catalyst for the highly chemoselective synthesis of α-amino acids by reductive aminatio

Synthesis and antioxidant properties of a new lipophilic ascorbic acid analogue

4-(4-Hydroxyphenyl)-5-(4-hydroxyphenylmethyl)-2-hydroxyfurane-2-one 1 was prepared by an acidic dimerisation of 4-hydroxyphenylpyruvic acid and some of its antioxidant and spectroscopic properties have been measured and compared to that of ascorbic acid. 1 is as good an antioxidant as ascorbic acid in the DPPH (2,2-diphenyl-1-picryl hydrazyl radical) test and the inhibition of hydroxyl radical and a powerful inhibitor of the Cu2+ or AAPH (2,2′-azobis-(2-amidinopropane) dihydrochloride) induced oxidation of human LDL. 1 gives a stable radical characterised by its ESR spectrum similarly to ascorbic acid but in lower concentration and with a different reactivity towards nitroxides. Theoretical calculations allow us to propose the structure for the radical formed from 1, to explain its lower stability than ascorbyl radical and to evaluate the lipophilicity of 1.

Process for production of phenyllactic acid derivative

A process for producing a phenyllactic acid derivative comprises hydrogenating a phenylpyruvic acid derivative in the presence of a catalyst containing at least one element selected from the Group VIII elements of the periodic table. The process provides a phenyllactic acid derivative useful as an intermediate in the production of pharmaceuticals and agricultural chemicals. The process uses as a starting material a phenylpyruvic acid derivative which is easily synthesized. The process is simpler in operation and provides a higher yield than conventional processes.

Selectivity and Specificity in Substrate Binding to Proteases: Novel Hydrolytic Reactions Catalysed by α-Chymotrypsin Suspended in Organic Solvents with Low Water Content and Mediated by Ammonium Hydrogen Carbonate

α-Chymotrypsin suspended in organic solvents with low water content catalysed hydrolytic reactions in the presence of ammonium hydrogen carbonate.Molecular modelling studies were carried out and structure-reactivity relationships were established by studying the hydrolysis of amino acid derivatives and analogues.The enzyme was found to be stereoselective with respect to the hydrolysis of L-amino acid derivatives, but no stereoselectivity was observed when α-hydroxy esters were used as substrates.A general procedure for the resolution of aromatic amino acid esters is given.The results are interpreted in terms of molecular modelling based on X-ray crystallographic data and literature data.

A modified synthesis of (±)-β-aryllactic acids

The synthesis of racemic forms of the reportedly active principle of Danshen, namely (±)-β-(3,4-dihydroxyphenyl)lactic acid [(±)3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid] and its seven racemic derivatives is reported.