(S)-(+)-Mandelic acid

Numéro de catalogue: B119166

Numéro CAS: 17199-29-0

Poids moléculaire: 152.15 g/mol

Clé InChI: IWYDHOAUDWTVEP-UHFFFAOYSA-N

Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.

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Vue d'ensemble

1. Description

7. Propriétés

2. Méthodes de préparation

8. Synthesis routes and methods I

3. Analyse des réactions chimiques

9. Synthesis routes and methods II

4. Applications de recherche scientifique

10. Retrosynthesis analysis

5. Mécanisme d'action

11. Q & A

6. Comparaison avec des composés similaires

12. Avertissement

Description

L’acide mandélique est un acide α-hydroxy aromatique de formule moléculaire C₆H₅CH(OH)CO₂H. Il se présente sous la forme d’un solide cristallin blanc soluble dans l’eau et les solvants organiques polaires. Le composé a été découvert en 1831 par le pharmacien allemand Ferdinand Ludwig Winckler lors du chauffage de l’amygdaline, un extrait d’amandes amères, avec de l’acide chlorhydrique dilué. Le nom « mandélique » dérive du mot allemand « Mandel », qui signifie amande .

Méthodes De Préparation

L’acide mandélique est généralement préparé par hydrolyse acidocatalysée du mandélonitrile, qui est la cyanhydrine du benzaldéhyde. Le mandélonitrile peut être synthétisé par réaction du benzaldéhyde avec le bisulfite de sodium pour former l’adduit correspondant, qui est ensuite traité avec du cyanure de sodium et hydrolysé . Industriellement, l’acide mandélique peut également être produit par hydrolyse basique de l’acide phénylchloroacétique ou de la dibromacétophénone . De plus, il peut être obtenu par chauffage du phénylglyoxal avec des alcalis .

Analyse Des Réactions Chimiques

L’acide mandélique subit diverses réactions chimiques, notamment :

Oxydation : L’acide mandélique peut être oxydé en acide benzoylformique en utilisant des agents oxydants tels que le permanganate de potassium.

Réduction : Il peut être réduit en acide phénylglycolique en utilisant des agents réducteurs comme le borohydrure de sodium.

Substitution : L’acide mandélique peut subir des réactions de substitution, telles que l’estérification avec des alcools en présence de catalyseurs acides pour former des esters.

Hydrolyse : L’hydrolyse du mandélonitrile en acide mandélique est une réaction courante, généralement réalisée en milieu acide.

Applications De Recherche Scientifique

L’acide mandélique a un large éventail d’applications en recherche scientifique :

Chimie : Il est utilisé comme agent de résolution chirale et comme précurseur dans la synthèse de divers produits pharmaceutiques.

Biologie : L’acide mandélique est impliqué dans la voie du mandélate, une série de réactions biochimiques chez certaines bactéries.

Médecine : Il est utilisé en dermatologie pour ses propriétés exfoliantes, antibactériennes et anti-inflammatoires.

Industrie : L’acide mandélique est utilisé dans la production d’agents antitumoraux et anti-obésité, ainsi que dans la fabrication de certains parfums et arômes.

Mécanisme D'action

L’acide mandélique agit en brisant les liaisons entre les cellules de la peau, ce qui conduit à un taux accru de renouvellement cellulaire. Ce mécanisme est bénéfique pour exfolier la peau et traiter des affections telles que l’acné, l’hyperpigmentation et les rides . Dans la voie du mandélate, des enzymes telles que la racémase du mandélate et la déshydrogénase du mandélate catalysent la conversion de l’acide mandélique en d’autres intermédiaires, facilitant sa dégradation et son utilisation dans le métabolisme bactérien .

Comparaison Avec Des Composés Similaires

L’acide mandélique est souvent comparé à d’autres acides α-hydroxy tels que l’acide glycolique et l’acide lactique. Contrairement à l’acide glycolique, qui a une taille moléculaire plus petite et pénètre plus rapidement dans la peau, l’acide mandélique a une taille moléculaire plus grande, ce qui se traduit par une pénétration plus lente et une irritation réduite . Des composés similaires incluent :

Acide glycolique : Connu pour ses fortes propriétés exfoliantes.

Acide lactique : Un autre acide α-hydroxy avec des avantages similaires à ceux de l’acide mandélique.

Acide citrique : Utilisé dans les soins de la peau pour ses propriétés exfoliantes et antioxydantes.

Les propriétés uniques de l’acide mandélique, telles que ses effets antibactériens et anti-inflammatoires, le rendent particulièrement adapté aux peaux sensibles et au traitement d’une variété d’affections dermatologiques .

Propriétés

IUPAC Name	2-hydroxy-2-phenylacetic acid	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	IWYDHOAUDWTVEP-UHFFFAOYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	C1=CC=C(C=C1)C(C(=O)O)O	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C8H8O3	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Related CAS	32518-00-6, Array	Source
Record name	Poly(mandelic acid)
Source	CAS Common Chemistry
URL	https://commonchemistry.cas.org/detail?cas_rn=32518-00-6
Description	CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society.
Explanation	The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.

Record name	Mandelic acid [USP]
Source	ChemIDplus
URL	https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000090642
Description	ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system.

DSSTOX Substance ID	DTXSID6023234	Source
Record name	Mandelic acid
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID6023234
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	152.15 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Physical Description	Liquid; Pellets or Large Crystals, Solid; Darkens and decomposes after prolonged light exposure; [Merck Index] White crystalline powder with a faint sweet odor; [Fisher Scientific MSDS]	Source
Record name	Benzeneacetic acid, .alpha.-hydroxy-
Source	EPA Chemicals under the TSCA
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Description	EPA Chemicals under the Toxic Substances Control Act (TSCA) collection contains information on chemicals and their regulations under TSCA, including non-confidential content from the TSCA Chemical Substance Inventory and Chemical Data Reporting.

Record name	Mandelic acid
Source	Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
URL	https://haz-map.com/Agents/15358
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Vapor Pressure	0.0000164 [mmHg]	Source
Record name	Mandelic acid
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Description	Haz-Map® is an occupational health database designed for health and safety professionals and for consumers seeking information about the adverse effects of workplace exposures to chemical and biological agents.
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CAS No.	90-64-2, 611-72-3	Source
Record name	Mandelic acid
Source	CAS Common Chemistry
URL	https://commonchemistry.cas.org/detail?cas_rn=90-64-2
Description	CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society.
Explanation	The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.

Record name	Mandelic acid [USP]
Source	ChemIDplus
URL	https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000090642
Description	ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system.

Record name	Mandelic acid
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URL	https://www.drugbank.ca/drugs/DB13218
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Record name	MANDELIC ACID
Source	DTP/NCI
URL	https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=7925
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Explanation	Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.

Record name	Benzeneacetic acid, .alpha.-hydroxy-
Source	EPA Chemicals under the TSCA
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Description	EPA Chemicals under the Toxic Substances Control Act (TSCA) collection contains information on chemicals and their regulations under TSCA, including non-confidential content from the TSCA Chemical Substance Inventory and Chemical Data Reporting.

Record name	Mandelic acid
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID6023234
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Record name	Mandelic acid
Source	European Chemicals Agency (ECHA)
URL	https://echa.europa.eu/substance-information/-/substanceinfo/100.001.825
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Record name	DL-2-hydroxy-2-phenylacetic acid
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URL	https://echa.europa.eu/substance-information/-/substanceinfo/100.009.344
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Record name	MANDELIC ACID
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Synthesis routes and methods I

Procedure details

To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor obtained from resolution B, containing about 2.4 moles of a mixture of diastereomers, consisting of about 2.25 moles of (-)-2-amino-1-butanol L-(+)-mandelate and about 0.15 mole of (-)-2-amino-1-butanol D-(-)-mandelate, is added 180 grams of potassium hydroxide (88.8% real; 2.85 moles) to obtain a solution having an initial αD25°C. of +24.7° ("as is", 10 cm cell). The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours to obtain a mandelic acid solution having an αD25°C. of -3.0° ("as is", 10 cm cell). The resulting solution is essentially racemized, the negative rotation being due to the presence of the (-)-2-amino-1-butanol.

[Compound]

Name

mixture

Quantity

2.4 mol

Type

reactant

Reaction Step One

Name

(-)-2-amino-1-butanol L-(+)-mandelate

Quantity

2.25 mol

Type

reactant

Reaction Step Two

Name

(-)-2-amino-1-butanol D-(-)-mandelate

Quantity

0.15 mol

Type

reactant

Reaction Step Three

Name

potassium hydroxide

Quantity

180 g

Type

reactant

Reaction Step Four

Name

mandelic acid

Details

Synthesis routes and methods II

Procedure details

To the filtrate remaining after process A above was added 201 grams of 50% sodium hydroxide solution, for a pH of 12.9. The basic solution was extracted 3 times with toluene, for a total toluene addition of 325 grams. The toluene and (-)PEA were distilled off under vacuum, resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams. The sodium mandelate/sodium acetate phase was neutralized with 305.4 grams HCl, giving a pH of about 0.8. This was extracted 4 times with MIBK, in a fashion similar to that above, for a total addition of 295.3 grams MIBK. 185 grams H2O was added to the MIBK, and the MIBK was distilled off with azeotropic distillation, returning 274.4 grams or 92.9% MIBK recovery. The mandelic acid recovered from this process, together with that recovered above, gave a total recovery of 299.44 grams mandelic acid, or an 89.5% return.

Name

sodium hydroxide

Quantity

201 g

Type

reactant

Reaction Step One

Name

sodium mandelate sodium acetate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

HCl

Quantity

305.4 g

Type

reactant

Reaction Step Three

Name

mandelic acid

Details

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.

Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

(S)-(+)-Mandelic acid

Reactant of Route 2

(S)-(+)-Mandelic acid

Reactant of Route 3

(S)-(+)-Mandelic acid

Reactant of Route 4

(S)-(+)-Mandelic acid

Reactant of Route 5

(S)-(+)-Mandelic acid

Reactant of Route 6

(S)-(+)-Mandelic acid

Customer

Q & A

Q1: What is the molecular formula and weight of (S)-mandelic acid?

A1: (S)-Mandelic acid has the molecular formula C8H8O3 and a molecular weight of 152.15 g/mol.

Q2: What spectroscopic techniques are typically used to characterize (S)-mandelic acid?

A2: Researchers utilize various spectroscopic techniques to characterize (S)-mandelic acid, including:

Nuclear Magnetic Resonance (NMR) spectroscopy: This technique provides detailed information about the compound's structure and stereochemistry. Researchers have employed ¹H NMR to determine enantiomeric excess using chiral solvating agents like (S)-mandelic acid. []
Circular Dichroism (CD) spectroscopy: This technique is specifically used to analyze chiral molecules like (S)-mandelic acid, providing insights into their absolute configuration and interactions with other chiral molecules. [, , ]

Q3: How stable is (S)-mandelic acid under different conditions?

A3: (S)-Mandelic acid exhibits varying stability depending on the environmental conditions:

Aqueous solutions: (S)-Mandelonitrile, a precursor to (S)-mandelic acid, exhibits improved stability in acidic aqueous solutions (pH < 5), mitigating spontaneous chemical hydrocyanation. []
Temperature and pressure: Research indicates that the conglomerate form of (S)-mandelic acid (crystals of separated enantiomers) becomes more stable than the racemic compound at higher pressures (approximately 0.64 GPa) and temperatures (460 K). []

Q4: What are the key catalytic applications of (S)-mandelic acid and its derivatives?

A4: (S)-Mandelic acid and its derivatives play crucial roles in various catalytic applications:

Chiral resolving agents: (S)-Mandelic acid effectively resolves racemic mixtures of amines and amino alcohols, yielding enantiomerically pure compounds. [, , , , ]
Chiral auxiliaries: Derivatives like (S)-mandelic acid esters act as efficient chiral auxiliaries in asymmetric synthesis, inducing diastereoselectivity in reactions like alkylations. [, , , ]
Chiral templates: (S)-Mandelic acid acts as a template for creating chiral cavities in materials like mesoporous platinum. This allows for enantioselective recognition and differentiation of chiral molecules. []

Q5: Can you provide an example of (S)-mandelic acid's use in enzymatic reactions?

A5: (S)-Mandelic acid serves as a substrate in the enzymatic resolution of racemic mandelic acid using immobilized lipases. This method offers a sustainable approach to obtaining enantiomerically pure (S)-mandelic acid and (R)-mandelamide. []

Q6: How is computational chemistry employed in research related to (S)-mandelic acid?

A6: Computational chemistry tools aid in understanding the properties and behavior of (S)-mandelic acid:

Molecular modeling: Researchers use molecular modeling to study the enantiospecific interactions of (S)-mandelic acid derivatives with chiral solutes, providing insights into observed asymmetric behavior. []
Density functional theory (DFT) calculations: These calculations help predict vibrational properties, such as IR and VCD spectra, for (S)-mandelic acid derivatives, assisting in stereochemical assignments. []

Q7: How do structural modifications of (S)-mandelic acid affect its activity?

A7: Modifying the structure of (S)-mandelic acid can significantly impact its properties and applications:

Esterification: Short-chain esters of (S)-mandelic acid, like (S)-n-propyl mandelate and (S)-isopropyl mandelate, exhibit distinct asymmetric behavior due to specific chiral interactions with solutes. []
Introduction of substituents: Modifying the phenyl ring of (S)-mandelic acid with halogens or hydroxyl groups can alter its binding affinity and selectivity towards specific targets. [, , ]

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Veuillez noter que tous les articles et informations sur les produits présentés sur BenchChem sont destinés uniquement à des fins informatives. Les produits disponibles à l'achat sur BenchChem sont spécifiquement conçus pour des études in vitro, qui sont réalisées en dehors des organismes vivants. Les études in vitro, dérivées du terme latin "in verre", impliquent des expériences réalisées dans des environnements de laboratoire contrôlés à l'aide de cellules ou de tissus. Il est important de noter que ces produits ne sont pas classés comme médicaments et n'ont pas reçu l'approbation de la FDA pour la prévention, le traitement ou la guérison de toute condition médicale, affection ou maladie. Nous devons souligner que toute forme d'introduction corporelle de ces produits chez les humains ou les animaux est strictement interdite par la loi. Il est essentiel de respecter ces directives pour assurer la conformité aux normes légales et éthiques en matière de recherche et d'expérimentation.

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