(S)-(+)-Mandelic acid
货号:
B119166
CAS 编号:
17199-29-0
分子量:
152.15 g/mol
InChI 键:
IWYDHOAUDWTVEP-UHFFFAOYSA-N
注意:
仅供研究使用。不适用于人类或兽医用途。
概述
描述
扁桃酸是一种芳香族α-羟基酸，分子式为C₆H₅CH(OH)CO₂H。它是一种白色结晶固体，可溶于水和极性有机溶剂。该化合物于1831年由德国药剂师费迪南德·路德维希·温克勒在将苦杏仁提取物扁桃苷与稀盐酸加热时发现。 “扁桃”一词源自德语“Mandel”，意思是杏仁 .
准备方法
扁桃酸通常通过苯甲醛的氰醇，即扁桃腈的酸催化水解制备。 扁桃腈可以通过使苯甲醛与亚硫酸氢钠反应生成相应的加合物合成，然后用氰化钠处理并水解 . 在工业上，扁桃酸也可以通过苯氯乙酸或二溴乙酰苯的碱水解来生产 . 此外，它可以通过加热苯基乙二醛与碱来获得 .
化学反应分析
扁桃酸会发生各种化学反应，包括：
氧化： 扁桃酸可以使用高锰酸钾等氧化剂氧化成苯甲酰甲酸。
还原： 它可以使用硼氢化钠等还原剂还原成苯基乙醇酸。
取代： 扁桃酸可以发生取代反应，例如在酸催化剂存在下与醇发生酯化反应生成酯。
科学研究应用
扁桃酸具有广泛的科学研究应用：
化学： 它用作手性拆分剂和各种药物合成的前体。
生物学： 扁桃酸参与扁桃酸途径，这是一系列发生在某些细菌中的生化反应。
作用机制
扁桃酸通过破坏皮肤细胞之间的键来起作用，导致细胞更新率增加。 这种机制有利于去除角质并治疗痤疮、色素沉着过度和皱纹等疾病 . 在扁桃酸途径中，扁桃酸消旋酶和扁桃酸脱氢酶等酶催化扁桃酸转化为其他中间体，促进其在细菌代谢中的降解和利用 .
相似化合物的比较
扁桃酸经常与其他α-羟基酸如乙醇酸和乳酸进行比较。 与乙醇酸不同，乙醇酸的分子量较小，渗透皮肤的速度更快，扁桃酸的分子量较大，导致渗透速度较慢，刺激性较低 . 类似的化合物包括：
乙醇酸： 以其强大的去角质特性而闻名。
乳酸： 另一种与扁桃酸具有类似益处的α-羟基酸。
柠檬酸： 因其去角质和抗氧化特性而用于护肤.
属性
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 | |
| URL | https://www.epa.gov/chemicals-under-tsca | |
| 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 | |
| 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. | |
| Explanation | Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission. | |
Vapor Pressure |
0.0000164 [mmHg] |
Source
|
| Record name | Mandelic acid | |
| Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
| URL | https://haz-map.com/Agents/15358 | |
| 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. | |
| Explanation | Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission. | |
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 | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB13218 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | MANDELIC ACID | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=7925 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
| 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 | |
| URL | https://www.epa.gov/chemicals-under-tsca | |
| 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 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | DL-2-hydroxy-2-phenylacetic acid | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.009.344 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | MANDELIC ACID | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/NH496X0UJX | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
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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
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 mandelate sodium acetate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
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.
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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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