4-羟基扁桃酸 | 1198-84-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-羟基扁桃酸
• 中文别名: DL-4-羟基扁桃酸单水化合物；对羟基扁桃酸
• 英文名称: 4-hydroxymandelic acid
• 英文别名: 2-hydroxy-2-(4-hydroxyphenyl)acetic acid；p-hydroxymandelic acid；4-Hydroxyphenylglycolic acid
• CAS: 1198-84-1
• 化学式: C₈H₈O₄
• 分子量: 168.149
• InChiKey: YHXHKYRQLYQUIH-UHFFFAOYSA-N

物化性质

• 熔点：
  82-85 °C(lit.)
• 沸点：
  405.4±30.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2918290000
• 安全说明：
  S26,S36
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  -20°C

SDS

Name:	DL-4-Hydroxymandelic acid 95% Material Safety Data Sheet
Synonym:	alpha,4-Dihydroxybenzeneacetic acid; DL-4-Hydroxymandelic acid; DL-p-Hydroxymandelic acid; p-Hydroxyphenylglycolic acid
CAS:	1198-84-1

Section 1 - Chemical Product MSDS Name:DL-4-Hydroxymandelic acid 95% Material Safety Data Sheet
Synonym:alpha,4-Dihydroxybenzeneacetic acid; DL-4-Hydroxymandelic acid; DL-p-Hydroxymandelic acid; p-Hydroxyphenylglycolic acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1198-84-1	4-Hydroxyphenylglycolic acid	95	214-839-7

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid breathing dust.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from light.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1198-84-1: CAS# 7198-10-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: off-white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 103-106 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H8O4
Molecular Weight: 168.15

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures. Darkens and decomposes on exposure to light.
Conditions to Avoid:
Dust generation, excess heat, excess light.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1198-84-1 unlisted.
CAS# 7198-10-9 unlisted.
LD50/LC50:
Not available.
Not available.
Carcinogenicity:
4-Hydroxyphenylglycolic acid - Not listed by ACGIH, IARC, or NTP.
Deleted Registry Number - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 1198-84-1: No information available.
CAS# 7198-10-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1198-84-1 is not listed on Canada's Ingredient Disclosure List.
CAS# 7198-10-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1198-84-1 is not listed on the TSCA inventory.
It is for research and development use only.
CAS# 7198-10-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

p-Hydroxymandelic acid 是一种有价值的芳香类化学品，广泛用于生产药物和食品添加剂。

靶点

Human Endogenous Metabolite

体外研究

p-Hydroxymandelic 酸 (4-Hydroxymandelic Acid; 4-HMA) 广泛应用于芳香类药物和香精的制备。它可用于合成 4-羟基苯乙酸，后者是选择性 β1 受体拮抗剂药物阿替洛尔的合成前体。p-Hydroxymandelic 酸还能与细胞毒性药物及酶底物结合，并在此基础上构建了一个适配系统，在靶向药物递送系统中显示出良好的应用前景。

化学性质

淡黄色水合物固体，熔点 95-97℃。

反应信息

• 作为反应物：
  描述：

  4-羟基扁桃酸 在 亚磷酸 、 甲烷磺酸 、 sodium iodide 作用下， 以 水 为溶剂， 反应 48.0h， 以62.2%的产率得到对羟基苯乙酸
  参考文献：
  名称：

  Iodide-Catalyzed Reductions: Development of a Synthesis of Phenylacetic Acids

  摘要：

  A new convenient and scalable synthesis of phenylacetic acids has been developed via the iodide catalyzed reduction of mandelic acids. The procedure relies on in situ generation of hydroiodic acid from catalytic sodium iodide, employing phosphorus acid as the stoichiometric reductant.

  DOI：

  10.1021/jo2018087
• 作为产物：
  描述：

  benzoyloxy-(4-benzoyloxy-phenyl)-acetonitrile 在 盐酸 、 sodium hydroxide 作用下， 生成 4-羟基扁桃酸
  参考文献：
  名称：

  Aloy; Rabaut, Bulletin de la Societe Chimique de France, 1912, vol. <4> 11, p. 390

  摘要：

  DOI：

文献信息

• Amino acid derivatives
  申请人：AstraZeneca AB

  公开号：US06337343B1

  公开（公告）日：2002-01-08

  There is provided amino acid derivatives of formula I, wherein p, q, R1, R2, R3, R4, Y, n and B have meanings given in the description which are useful as competitive inhibitors of trypsin-like proteases, such as thrombin, and in particular in the treatment of conditions where inhibition of thrombin is required (e.g. thrombosis) or as anticoagulants.

  提供的是公式I的氨基酸衍生物，其中p、q、R1、R2、R3、R4、Y、n和B具有本说明书中给出的含义，它们可用作胰蛋白酶样蛋白酶（如凝血酶）的竞争性抑制剂，特别是在需要抑制凝血酶的情况（例如血栓形成）的治疗中，或者作为抗凝剂。
• PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
  申请人：Philippe Michel

  公开号：US20100028280A1

  公开（公告）日：2010-02-04

  The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

  该发明涉及一种直发角蛋白纤维的拉直过程，包括：(i)将至少两种变性剂含有的拉直组合物涂抹到角蛋白纤维上的步骤，(ii)使用加热装置将角蛋白纤维的温度升高至110至250°C的步骤。
• Hypervalent iodine in organic synthesis. A new route to α-functionalized carboxylate esters.
  作者：Robert M. Moriarty、Henry Hu

  DOI：10.1016/s0040-4039(01)90541-6

  日期：1981.1

  Aryl and alkylcarboxylate esters are converted into the corresponding α-hydroxy acids or α-alkoxyesters upon treatment with C6H5I(OAc)2 and base in the appropriate solvent.

  在合适的溶剂中用C 6 H 5 I（OAc）2和碱处理后，芳基和烷基羧酸酯转化为相应的α-羟基酸或α-烷氧基酯。
• The Reaction between Hydrogen Spiro-Borates and Carbinol Form of Crystal Violet in Toluene with Applications to Reagent Selection in Extraction-Spectrophotometry of Boron
  作者：Susanta K. Sengupta、O. Balasubramanian

  DOI：10.1246/bcsj.64.1437

  日期：1991.4

  A study on equilibrium and kinetics of the reactions of boron complexes of a judiciously chosen series of hydroxy and dicarboxy acids (benzilic acid, mandelic acid, 3-chloro- and 4-hydroxy mandelic acid, salicylic acid, and phenylmalonic acid) as well as of the free acids with carbinol form of crystal violet in toluene demonstrated the distinct superiority of mandelic acid over the others, as a reagent for extraction-photometry of boron.

  对于选择的一系列羟基和二羧酸（苄基酸、扁桃酸、3-氯扁桃酸、4-羟基扁桃酸、水杨酸和苯基丙二酸）的硼配合物以及自由酸与甲苯中醇型结晶紫反应的平衡和动力学研究表明，扁桃酸作为硼的萃取光度法试剂，其优势明显优于其他酸。
• Novel sulfonyldiazomethanes, photoacid generators, resist compositions, and patterning process
  申请人：——

  公开号：US20040167322A1

  公开（公告）日：2004-08-26

  A chemical amplification type resist composition comprising a specific benzenesulfonyldiazomethane containing a long-chain alkoxyl group at the 2-position on benzene ring has many advantages including improved resolution, improved focus latitude, minimized line width variation or shape degradation even on long-term PED, minimized debris left after coating, development and peeling, and improved pattern profile after development and is thus suited for microfabrication.

  一种化学放大型抗蚀组合物，包括在苯环上的2-位含有长链烷氧基基团的特定苯磺酰二氮甲烷，具有许多优点，包括提高分辨率，改善焦点宽度，即使在长期PED上也减少线宽变化或形状退化，涂层、显影和剥离后减少残留物，并在显影后改善图案轮廓，因此适用于微加工。