Coumarin 香豆素

CAS 91-64-5 MFCD00006850

化学结构图

91-64-5
SMILES: O=C1CCC2CCCCC2O1

化学属性

Mol. FormulaC9H6O2
Mol. Weight146.14
Density0.935
Boiling Point297.999 °C at 760 mmHg
Vapor Pressure0.01 mmHg ( 47 °C)
Melting Point68-73 °C
Flash Point162°(323°F)
TSCAYes
Stability对湿度敏感
Appearance 具有升华性的白色性结晶,有香茅香气,并略有药香香韵。 不溶于冷水,溶于热水、乙醇、乙醚、氯仿。
Solubility1.7 g/L (20 °C)

别名和识别编码

Chemical NameCoumarin
MDL NumberMFCD00006850
CAS Number91-64-5
EC Number202-086-7
Beilstein Registry Number17,328
Synonym Coumarin {LY} Coumarin {} {LY} Coumarin {} {} {LY} Coumarin {} {} {} {LY} Coumarin {} {} {} {} {LY} Coumarin {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Coumarin {} {} {} {} {} {} {} {} {} {
PubChem Substance ID323
Merck Number2562
Chemical Name Translation香豆素
Reaxys-RN383644
Wiswesser Line NotationT66 BOVJ
LabNetwork Molecule IDLN00238124
InChIInChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
Canonical SMILESO=C1C=CC2=CC=CC=C2O1
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分类

  • {SNA} Alphabetical Listings, Bioactive Small Molecules, C-D, CI-CY, Flavors and Fragrances, 细胞生物学
  • {SNA} 2009/48/EC
  • {SNA} Alphabetical Listings, Bioactive Small Molecules, C-D, CI-CY, Cell Biology, Flavors and Fragrances
  • {SNA} Analytical Standards,
  • {SNA} Analytical Standa
  • {SNA} A - D, Alphabetical Listings, C-D, Essential Oils, Flavors and Fragrances, Halal Certified Products
  • {SNA} A - D, A-F, All Alphabetically Sorted, Alphabetical, Analytical Standards, Analytical/Chromatography, Beans, Chromatography,

产品应用

  • 荧光指示剂。

相关文献及参考

  • Merck: 14,2562 Beilstein:17,328
  • Merck: 14,2562

安全信息

Signal word Danger Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • 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;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • 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;
  • S36/37/39 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;
Risk Statements
  • R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R22 Harmful if swallowed 吞咽有害
  • 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
Precautionary statements
  • P301+P310+P330
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P405 Store locked up. 上锁保管。
  • P301+P310
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
Hazard statements
  • H301 Toxic if swallowed 吞食有毒
RTECSGN4200000
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Packing GroupIII
UN Number UN 2811 6.1/PG 3 UN2811 2811
Hazard Codes Xn
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 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Hazard Class6.1
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 144 gm/kg/2Y-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Lungs, Thorax, or Respiration - bronchiogenic carcinoma
REFERENCE :
   NTPTR* National Toxicology Program Technical Report Series.  (Research
   Triangle Park, NC 27709) No.206-  Volume(issue)/page/year: NTP-TR-422,1993

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 18025 mg/kg/2Y-I
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Kidney, Ureter, Bladder - Kidney tumors
REFERENCE :
   NTPTR* National Toxicology Program Technical Report Series.  (Research
   Triangle Park, NC 27709) No.206-  Volume(issue)/page/year: NTP-TR-422,1993

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 200 gm/kg/2Y-C
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Liver - tumors
REFERENCE :
   TXCYAC Toxicology.  (Elsevier Scientific Pub. Ireland, Ltd., POB 85,
   Limerick, Ireland) V.1-    1973-  Volume(issue)/page/year: 1,93,1973

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - guinea pig
DOSE/DURATION           : 202 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Liver - other changes
REFERENCE :
   FCTXAV Food and Cosmetics Toxicology.  (London, UK)  V.1-19, 1963-81.  For
   publisher information, see FCTOD7.  Volume(issue)/page/year: 2,327,1964

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 30 mg/kg/30D-I
TOXIC EFFECTS :
   Liver - liver function tests impaired
REFERENCE :
   HUTODJ Human Toxicology.  (Macmillan Press Ltd., Houndmills, Basingstoke,
   Hants., RG 21 2XS, UK) V.1-    1981-  Volume(issue)/page/year: 8,501,1989

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 196 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YKKZAJ Yakugaku Zasshi.  Journal of Pharmacy.  (Nippon Yakugakkai, 2-12-15
   Shibuya, Shibuya-ku, Tokyo 150, Japan)  No.1-    1881-
   Volume(issue)/page/year: 83,1124,1963

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 220 mg/kg
TOXIC EFFECTS :
   Behavioral - analgesia
   Biochemical - Enzyme inhibition, induction, or change in blood or tissue
   levels - true cholinesterase
REFERENCE :
   ARZNAD Arzneimittel-Forschung. Drug Research.  (Editio Cantor Verlag,
   Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.)  V.1-    1951-
   Volume(issue)/page/year: 15,897,1965

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Mammal - species unspecified Lymphocyte
DOSE/DURATION           : 20 mmol/L
REFERENCE :
   PNASA6 Proceedings of the National Academy of Sciences of the United States
   of America.  (National Academy of Sciences, Printing & Pub. Office, 2101
   Constitution Ave., Washington, DC 20418) V.1-    1915-
   Volume(issue)/page/year: 48,686,1962

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 1600 mg/L
REFERENCE :
   EMMUEG Environmental and Molecular Mutagenesis.  (Alan R. Liss, Inc., 41 E.
   11th St., New York, NY 10003)  V.10-    1987-  Volume(issue)/page/year:
   10(Suppl 10),1,1987

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 100 mg/L
REFERENCE :
   EMMUEG Environmental and Molecular Mutagenesis.  (Alan R. Liss, Inc., 41 E.
   11th St., New York, NY 10003)  V.10-    1987-  Volume(issue)/page/year:
   10(Suppl 10),1,1987

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 1 mg/plate
REFERENCE :
   ENMUDM Environmental Mutagenesis.  (New York, NY)  V.1-9, 1979-87.  For
   publisher information, see EMMUEG.  Volume(issue)/page/year: 5(Suppl
   1),3,1983

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 3600 mg/kg
SEX/DURATION            : female 6-17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   ARZNAD Arzneimittel-Forschung. Drug Research.  (Editio Cantor Verlag,
   Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.)  V.1-    1951-
   Volume(issue)/page/year: 17,97,1967

其他信息

  • 图谱信息:香豆素(91-64-5)质谱(MS) 香豆素(91-64-5)红外图谱(IR3) 香豆素(91-64-5)核磁图( 13 CNMR) 香豆素(91-64-5)红外图谱(IR2) 香豆素(91-64-5)红外图谱(IR1) 香豆素(91-64-5)核磁图( 1 HNMR) 香豆素(91-64-5)Raman光谱
  • 有香荚兰豆香,味苦,能溶于醇、醚、氯仿、吡啶、挥发油和氢氧化碱溶液中,微溶于沸水。
  • 下游产品:氧茚 --> 溴敌隆 --> 4-氨基-N,N-二甲基苯胺 --> 香豆素 7 --> 氢化肉桂酸内酯
  • 方法一:(1)由水杨醛经珀金(Perkin)反应制得。这是珀金在1868年最初采用的合成方法。水杨醛与乙酐反应可以使用煅烧的碳酸钾作为催化剂。将碳酸、乙酐加入水杨醛中,加热至187℃,在气相温度约120℃时蒸出乙酸,然后再加入乙酐,在210-212℃进行反应。得到的香豆素粗品用水洗涤,再真空蒸馏。然后用乙醇或异丙醇重结晶,在50℃干燥得成品。(2)由邻甲酚与磷酰氯作用,得到中间体邻甲酚磷酸酯,并在180℃氯化,将甲基变为-CHCI2,然后再在160-180℃与醋酸钠作用5h进行环化即得。如果邻甲酚与光气作用,则经由中间体邻甲酚碳酸酯而完成这一工艺过程:邻甲酚钠盐与光气在60℃、0.15MPa下反应生成邻甲酚碳酸酯。用氯气在180-185℃将酯化进行氯化,至含氯量约为37%,相当于每个甲酚的侧链上含有两个氯原子。最后,在吡啶或氧化锌和氧化钴存在下,与乙酸和乙酐缩合,反应得到香豆素,该法收率相当高。
  • 灭火剂:水, 二氧化碳, 干粉, 砂土
  • Alfa Aesar:邻氧萘酮,98% Coumarin, 98%(91-64-5)
  • MOL 文件:91-64-5.mol
  • Sigma Aldrich:91-64-5(sigmaaldrich)
  • TCI Shanghai:香豆素 Coumarin,>;99.0%(GC)(91-64-5)
  • 类别:有毒物质
  • 用途二:用于制造香料,作为定香剂,也用于电镀工业
  • 蒸气压:0.01 mm Hg ( 47 °C)
  • 香豆素价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 69009228 香豆素;1,2-苯并吡喃酮; 1,2-苯并哌哢; 氧杂萘邻酮; 香豆内酯; 苯并邻氧芑酮 500g 96元 2011/04/16 C0395 香豆素 Coumarin 25G 164元 2011/04/16 C0395 香豆素 Coumarin 500G 818元
  • 上游原料:三氯氧磷 --> 醋酸钠 --> 2-羟基苯甲醛 --> 邻甲酚 --> 磷酸酯
  • 检测方法:HPLC
  • 用途一:用于香精和香皂的制造
  • 用途四:荧光指示剂。
  • 急性毒性:口服- 大鼠 LD50 293 毫克/ 公斤; 口服- 小鼠 LD50: 196 毫克/公斤
  • 毒性分级:高毒
  • 储运特性:库房低温, 通风, 干燥; 与食品原料分开存放
  • 用途三:香豆素是于1820年在黑香豆中发现的。香豆素以苷的形式存在于许多植物中。具有黑香豆的浓重香味,亦具有新刈草甜香及巧克力气息,留香长久。新鲜的干草香气在很大程度上是由于在干燥新刈草过程中,苷在发酵分解时生成并释出香豆素所引起的。香豆素用于制造香料。常用在配制新刈草型及馥奇型香料。以及紫罗兰、葵花、素心兰、山楂花、兰花、薰衣草等香精中。它和香兰素一起可用于糖果、糕点之类有调味,加入烟草中可以增加天然香味。在镀锌(或镉、镍)的电镀液中加入香豆素,可减少镀层起孔,增加光亮度。香豆素是制造其他香料和多种其他化学品的原料。香豆是一大类衍生物的母体。这些衍生物中有些存在于自然界,有些则通过合成方法制得。
  • Acros Organics:香豆素 Coumarin, 99+%(91-64-5)
  • 可燃性危险特性:可燃; 火场分解有毒氮氧化物烟雾

系列性分类


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