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羟基乙酸

羟基乙酸用途

Glycolic Acid 是酪氨酸酶 (tyrosinase) 的抑制剂,能抑制黑色素的形成,从而减淡皮肤的颜色。

羟基乙酸名称

[ CAS 号 ]:
79-14-1

[ 中文名 ]:
羟基乙酸

[ 英文名 ]:
Glycolic acid

[中文别名 ]:

[英文别名 ]:

Glycocide
QV1Q
CHC-22
2-Hydroxyethanoic acid
Acetic acid, 2-hydroxy-
GlyPure 99
hydroxyacetic acid
HOCH2COOH
Glykolsure
Glycol acid

羟基乙酸生物活性

[ 描述 ]:

Glycolic Acid 是酪氨酸酶 (tyrosinase) 的抑制剂,能抑制黑色素的形成,从而减淡皮肤的颜色。

[ 相关类别 ]:

信号通路 >> 代谢酶/蛋白酶 >> 酪氨酸酶

天然产物 >> 其他

研究领域 >> 代谢疾病

[ 靶点 ]

Human Endogenous Metabolite

[体外研究]

测试不同浓度的乙醇酸(GA)或LA(300和500mg/mL)对小鼠和人黑素瘤细胞的生长。两种类型的细胞生长良好,即使在300mg/mL的每种化学品存在下持续5天。然而,500 mg/mL乙醇酸抑制小鼠黑色素瘤细胞(41％)和人黑色素瘤细胞(27％)的细胞生长,500 mg/mL的LA抑制小鼠黑色素瘤细胞的生长(36％)[1]。

[细胞实验]

HM3KO着色的人黑素瘤细胞和B16小鼠黑素瘤细胞在补充有10％胎牛血清的Dulbecco改良的Eagles培养基中培养，并将适量的抗生素和杀菌剂以100mg / mL的浓度溶解在蒸馏水中。将这些化学物质（例如乙醇酸）以每2天300或500 mg / mL的最终浓度添加到细胞培养物中，持续5天[1]。

[参考文献]

[1]. Usuki A, et al. The inhibitory effect of glycolic acid and lactic acid on melanin synthesis in melanoma cells. Exp Dermatol. 2003;12 Suppl 2:43-50.

[相关活性小分子]

羟基乙酸物理化学性质

[ 密度 ]:
1.4±0.1 g/cm3

[ 沸点 ]:
265.6±13.0 °C at 760 mmHg

[ 熔点 ]:
75-80 °C(lit.)

[ 分子式 ]:
C₂H₄O₃

[ 分子量 ]:
76.051

[ 闪点 ]:
128.7±16.3 °C

[ 精确质量 ]:
76.016045

[ PSA ]:
57.53000

[ LogP ]:
-1.05

[ 外观性状 ]:
淡黄色至琥珀色液体

[ 蒸汽压 ]:
0.0±1.2 mmHg at 25°C

[ 折射率 ]:
1.450

[ 储存条件 ]:
2-8°C

[ 稳定性 ]:
Stable. Incompatible with bases, oxidizing agents and reducing agents.

[ 水溶解性 ]:
SOLUBLE

羟基乙酸MSDS

羟基乙酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MC5250000

CHEMICAL NAME :: Glycolic acid

CAS REGISTRY NUMBER :: 79-14-1

BEILSTEIN REFERENCE NO. :: 1209322

LAST UPDATED :: 199801

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C2-H4-O3

MOLECULAR WEIGHT :: 76.06

WISWESSER LINE NOTATION :: QV1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: AJOPAA American Journal of Ophthalmology. (Ophthalmic Pub. Co., 435 N. Michigan Ave., Suite 1415, Chicago, IL 60611) Series 3: V.1- 1918- Volume(issue)/page/year: 29,1363,1946 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1950 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - other changes Kidney, Ureter, Bladder - other changes

REFERENCE :: JIHTAB Journal of Industrial Hygiene and Toxicology. (Cambridge, MA) V.18-31, 1936-49. For publisher information, see AEHLAU. Volume(issue)/page/year: 23,259,1941

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85JCAE "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986 Volume(issue)/page/year: -,656,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 1920 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - other changes Kidney, Ureter, Bladder - other changes

REFERENCE :: JIHTAB Journal of Industrial Hygiene and Toxicology. (Cambridge, MA) V.18-31, 1936-49. For publisher information, see AEHLAU. Volume(issue)/page/year: 23,259,1941 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2480 gm/kg/35W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: ABBIA4 Archives of Biochemistry and Biophysics. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.31- 1951- Volume(issue)/page/year: 84,183,1959

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 gm/m3/6H/2W-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0546415 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 9 gm/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 53,117,1996 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 35260 No. of Facilities: 2991 (estimated) No. of Industries: 27 No. of Occupations: 29 No. of Employees: 29291 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 35260 No. of Facilities: 5782 (estimated) No. of Industries: 64 No. of Occupations: 63 No. of Employees: 191563 (estimated) No. of Female Employees: 98538 (estimated)

羟基乙酸安全信息

[ 符号 ]:

GHS05, GHS07

[ 信号词 ]:
Danger

[ 危害声明 ]:
H314-H332

[ 警示性声明 ]:
P261-P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338

[ 个人防护装备 ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ 危害码 (欧洲) ]:
C:Corrosive

[ 风险声明 (欧洲) ]:
R22;R34

[ 安全声明 (欧洲) ]:
S26-S36/37/39-S45-S23

[ 危险品运输编码 ]:
UN 3265 8/PG 3

[ WGK德国 ]:
1

[ RTECS号 ]:
MC5250000

[ 包装等级 ]:
II

[ 危险类别 ]:
8

[ 海关编码 ]:
2918199090

羟基乙酸合成路线

羟基乙酸上下游产品

羟基乙酸上游产品

羟基乙酸下游产品

羟基乙酸制备

1.氯乙酸法氯乙酸在碱性条件下水解得粗品，然后经甲醇酯化得羟基乙酸甲酯，蒸馏后再水解即得成品。

2.高温高压法由甲醛、二氧化碳和水反应制得。

3.甲醛与氢氰酸于常压0～50℃下，在弱碱性或弱酸性条件下发生反应，所得氰基甲醇再于酸性条件下水解，控制反应温度大于90℃，反应结束后，采用萃取和结晶法进行提纯，即可得成品。
过程反应式：

4.氰化钠法以甲醛、氰化钠为原料，经加氰和酸性水解两步制得。

5.由氯乙酸与氢氢化钠反应，在硫酸作用下，用甲醇酯化，再水解，经减压蒸馏回收甲醇得到羟基乙酸成品。或者甲醛和一氧化碳在硫酸或三氟化硼等酸性催化剂存在下，缩合生成羟基乙酸。

6．将氯乙酸溶液加热至85℃，加入氢氧化钠溶液进行反应，维持温度95～98℃48H，之后，除去氯化
钠并减压浓缩得胶脂，再加热回流至胶脂完全溶于甲醇，蒸出剩余甲醇后，减压蒸馏得羟基乙酸乙酯，再进行水解，减压蒸馏至含量合格。
过程反应式为：

7. 烟草：FC，54；BU，26。

羟基乙酸海关

[ 海关编码 ]: 2918199090

[ 中文概述 ]:
HS: 2918199090. 其他含醇基但不含其他含氧基羧酸（包括其酸酐、酰卤化物、过氧化物和过氧酸及该税号的衍生物）. 增值税率:17.0%. 退税率:9.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途

[ Summary ]:
2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

羟基乙酸文献

Safety and biocompatibility of carbohydrate-functionalized polyanhydride nanoparticles.

AAPS J. 17(1) , 256-67, (2015)

Carbohydrate functionalization of nanoparticles allows for targeting of C-type lectin receptors. This family of pattern recognition receptors expressed on innate immune cells, such as macrophages and ...

Physiology and pathophysiology of organic acids in cerebrospinal fluid.

J. Inherit. Metab. Dis. 16(4) , 648-69, (1993)

Concentrations of organic acids in cerebrospinal fluid (CSF) appear to be directly dependent upon their rate of production in the brain. There is evidence that the net release of short-chain monocarbo...

HMDB: a knowledgebase for the human metabolome.

Nucleic Acids Res. 37(Database issue) , D603-10, (2009)

The Human Metabolome Database (HMDB, http://www.hmdb.ca) is a richly annotated resource that is designed to address the broad needs of biochemists, clinical chemists, physicians, medical geneticists, ...

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