CAS 501-30-4 MFCD00006580-Kojic Acid 曲酸 TAO{mole}

Kojic Acid 曲酸

CAS 501-30-4 MFCD00006580

化学结构图

SMILES: O=c1cc(CO)occ1O

化学属性

Mol. Formula	C6H6O4
Mol. Weight	142.11
Melting Point	152-155°C
TSCA	No
Solubility	一种黑色素专属性抑制剂，溶于水，易溶于丙酮和乙醇，微溶于乙醚、乙酸乙酯、氯仿和吡啶；不溶于苯。
Density	1.542
Boiling Point	401.7°C at 760 mmHg

别名和识别编码

Chemical Name	Kojic Acid
Synonym	Kojic acid {LY} Kojic acid {} {LY} Kojic acid {} {} {LY} Kojic acid {} {} {} {LY} Kojic acid {} {} {} {} {LY} Kojic acid {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {} {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Kojic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Kojic acid
MDL Number	MFCD00006580
PubChem Substance ID	87571949
Beilstein Registry Number	120895
CAS Number	501-30-4
EC Number	207-922-4
Merck Number	5317
Chemical Name Translation	曲酸
Reaxys-RN	120895
InChIKey	BEJNERDRQOWKJM-UHFFFAOYSA-N
Wiswesser Line Notation	T6O DVJ B1Q EQ
LabNetwork Molecule ID	LN00195082
InChI	InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2
Canonical SMILES	O=C1C=C(CO)OC=C1O

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分类

{SNA} All alphabetically sorted, Alphabetical Index of Analytical Standards, Analytical Standards, Antioxidants & Preservatives, Biotoxins, Chromatography, K, Life Sciences Standards, Mycotoxins, Neat, Other, Pesticides, Bactericides, Fungicides and Disinfectants, Standards for Personal Care and Cosmetic Products, 分析/色谱
{SNA} Bioactive Small Molecules, Building Blocks, Cell Biology, Chemical Synthesis, Heterocyclic Building Blocks, K, Pyrans
{SNA} Bioactive Small Molecule Alphabetical Index, Enzyme Inhibitors, K, Neuroscience, Neurotr

产品应用

用作定量分析三价铁的试剂。
酪氨酸酶抑制剂。曲菌酸是一种黑色素专属性抑制剂，它进入皮肤细胞后能够与细胞中的铜离子络合，改变酪氨酸酶的立体结构，阻止酪氨酸酶的活化，从而抑制黑色素的形成。存在于酿酒用的曲霉（Aspergillus）培养基中。可利用米曲霉（Aspergillus oryzae）进行好氧发酵制取。用作增香剂。

安全信息

WGK Germany3

RTECSUQ0875000

Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Safety Statements

S22 Do not breathe dust 不要吸入粉尘；
S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；

Risk Statements

R45 May cause cancer 可能致癌
R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
R42/43
R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
R68 Possible risk of irreversible effects 可能有不可挽回的作用的危险

Hazard Codes T;Xn

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 250 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- ,  Berdy, J., Boca
   Raton, FL, CRC Press, 1980-  Volume(issue)/page/year: 5,393,1981

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1500 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - convulsions or effect on seizure threshold
   Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
   NATUAS Nature.  (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736)
   V.1-    1869-  Volume(issue)/page/year: 155,302,1945

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Mammal - dog
DOSE/DURATION           : 1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al.,
   eds., Washington, DC, American Soc. for Microbiology, 1978
   Volume(issue)/page/year: 3,1755,1978

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al.,
   eds., Washington, DC, American Soc. for Microbiology, 1978
   Volume(issue)/page/year: 3,1755,1978

{ha

TYPE OF TEST            : LDLo - Lowest publ

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 2 mg/plate
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 67,367,1979

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 4500 mg/L
REFERENCE :
   TOLED5 Toxicology Letters.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1977-  Volume(issue)/page/year: 59,213,1991

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 4500 mg/L
REFERENCE :
   TOLED5 Toxicology Letters.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1977-  Volume(issue)/page/year: 59,213,1991

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 500 ng/plate
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 58,193,1978

GHS Symbol

Precautionary statements

P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。

Storage condition 2-8°C {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {

其他信息

应用与用途:(1) 曲酸在食品生产中有非常广泛的应用。以往曲酸由于有抗氧化性曾用于油脂防止酸败，近年来的文献报道，曲酸有杀菌抗虫作用，作为食品的防腐剂、保鲜剂、护色剂使用有明显的效果，可替代化学防腐剂广泛用于肉食品加工护色、果蔬保鲜、生食品的杀菌防腐中，还可用作切花保持剂延长鲜花保存及货架期等。食品中添加曲酸，既不会影响其本身的口味、香味及质感，又能阻碍亚硝酸盐转化成对人体有致癌危害的亚硝胺，这种阻碍或抑制作用，对腌腊肉制品类产品的换代升级有着非常重要的意义。农业生产方面，曲酸既可用作生物农药，用作杀虫剂，又可用作生物肥料，不论喷施还是根施，对粮食和蔬菜的增产增收效果显著。 (2) 作为食品增香剂麦芽酚和乙基麦芽酚
有机酸:曲酸又称曲菌酸、鞠酸，是由葡萄糖经曲霉念珠菌在30～32℃下好氧发酵产生的具有抗菌作用的有机酸，分子结构为带取代基的γ-吡喃酮，在自然界存在的γ-吡喃酮化合物中，著名的化合物只有曲酸和麦芽酚。1907年Saito由米曲中分离出曲酸结晶。1912年由Yabuta命名并于1924年确定其结构。1953年Arnstela(表面发酵)和1971年北田牧夫(深层发酵)运用同位素追踪技术证明曲酸是葡萄糖未经碳架断裂直接氧化、脱水形成的。曲酸存在于曲中，它是人们食用的东西，使用安全。近年来，大量的专利文献报道曲酸在化妆品中的应用。酪氨酸酶是生成黑色素的关键酶。曲酸能与酪氨酸酶的铜螯合而使之失去活性，这是其美白作用的基础。临床和应用试验结果表明，曲酸对人体皮肤的黑色素生成有较强的抑制作用，而且安全，无毒，不会引起白斑后遗症。曲酸与其它制剂(如SOD，胎盘提取物、氨基酸、防晒剂和各类植物提取物等)复配使用效果更好。曲酸主要用于皮肤增白制品、抗衰老制品、防晒制品、增白洗面奶和美容化妆品。曲酸具有一定的抗菌活性。革兰氏阴性细菌对曲酸钠的敏感程度大于革兰氏阳性细菌，而大多数其他抗菌物质则相反。曲酸的抑菌作用远低于其他抗菌物质，其抗菌活性是抑菌性而非杀菌性。曲酸对酵母、病毒和噬菌体无效。以上信息由Chemicalbook的彤彤编辑整理。
{Chem
曲酸的提取及精制:曲酸与2价金属离子可形成难溶性的金属螯合物，这一性质可在提取时利用。其次，曲酸虽然溶于水但溶解度不大，温度对其溶解度影响很大，有利于浓缩降温结晶。曲酸可作为铁试剂。即使使用不锈钢发酵罐，其发酵液也呈红褐色，这一性质影响到提取、精制过程。从发酵液中提取曲酸曾用过铜盐沉淀法、醋酸乙酯萃取法、乙醚连续萃取法、浓缩结晶或冷冻结晶法等。20世纪70年代，北京日化一厂使用锌盐法。
微生物发酵法制曲酸:微生物发酵法制曲酸是指用微生物发酵法大量生产曲酸的工艺和技术。曲酸是由米曲霉等微生物产生的一种酸性代谢产物，能溶于水、乙醇或醋酸酯等。能产生曲酸的微生物多数为真菌，如米曲霉(Aspergillus oryzae)、米黄曲霉 (A.flavo-oryzae)、黄曲霉(A.flavus)、亮白曲霉(A.candidus)、棒曲霉(A. clavatus)、巨大曲霉(A.giganteus)、烟曲霉(A.fumigatus)、溜曲霉(A.tamarii)、温特曲霉(A.wentii)和灰绿曲霉(A.glaucus)等。某些细菌如玫瑰葡糖杆菌 (Gluconobacter roseus)、蜡状葡糖杆菌(G.cerinus)和若干假单胞菌(Pseudomonas spp)也可利用糖类生成曲酸。基本发酵工艺为：甘薯粉经α-淀粉酶水解→灭菌→在发酵罐中冷却→接种米曲霉种子(来自种子罐)→32℃左右通气发酵(约5天)→发酵液抽滤→制成曲酸的锌盐→减压浓缩→结晶→酸化→曲酸。曲酸是用于制造食品和日用品中的增香剂麦芽酚和乙基麦芽酚的原料，也是生产杀虫剂、杀菌剂和胶片脱尘剂的原料，若与某些脂肪族羧酸发生酰化，就可获得曲酸酯，它是制造增白化妆品的原料。参考资料：周德庆,徐士菊编著.微生物学词典.天津：天津科学技术出版社.2005.
美白化妆品和美白食品中添加曲酸:曲酸为酪氨酸酶抑制剂，能抢先与酪氨酸酶中的铜离子熬合，使铜离子失去作用，进而抑制多巴色素的合成。曲酸能抑制5，6-二羟基吲哚(DHI)聚合，抑制DHICA氧化酶的活性。添加曲酸的化妆品有护肤、润肤、美白、光亮、防晒、祛斑的功能。剂型有膏霜、洗剂、乳液、软膜粉、泥胶、粉饼等。国内最早 (1987年) 研制并获得卫生部批准文号 (1991年) 的是南京石山头制药厂的142-曲酸祛斑霜，其曲酸含量有1.5%、2.0%两种规格。主要用于治疗各