Trans-Anethole 反式-茴香醚

CAS 4180-23-8 MFCD00009284

化学结构图

4180-23-8
SMILES: C/C=C/c1ccc(OC)cc1

化学属性

Mol. FormulaC10H12O
Mol. Weight148.20
Refractive indexn20/D 1.561(lit.)
Boiling Point237.5°C at 760 mmHg
Density0.987
Melting Point20-21°C
Flash Point91°C
TSCAYes
Appearance 茴香脑(104-46-1)为无色或微黄色液体或结晶。熔点为22.5℃,沸点235℃,81-81.5℃(307Pa),相对密度0.9883(20/4℃),折光率1.56145,闪点90℃。能与氯仿、醚混溶,溶于苯、乙酸乙酯、丙酮、二硫化碳、石油醚和醇,不溶于水。带有甜味,具茴香的特殊香气。 天然品存在于茴香油、八角茴香油、茴芹油等中。 白色晶体,23℃以上时为无色或极微黄色液体。呈茴香似香气,有甜味。遇光、热、空气易变质。用KMnO4氧化,生成对大茴香酸(熔点184℃)。凝固点21~22℃,熔点22.5~23℃,沸点234℃,闪点92.2℃。溶于乙醇和油类,微溶于水,混溶于氯仿和乙醚,几不溶于甘油和丙二醇。
Solubilitypractically insoluble

别名和识别编码

Chemical NameTrans-Anethole
Synonym Trans-Anethole {LY} Trans-Anethole {} {LY} Trans-Anethole {} {} {LY} Trans-Anethole {} {} {} {LY} Trans-Anethole {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Trans-Anethole {} {} {} {} {} {} {} {} {} {} {} {} {
CAS Number4180-23-8
PubChem Substance ID637563
EC Number224-052-0
Beilstein Registry Number774229
MDL NumberMFCD00009284
Merck Number643
Reaxys-RN636190
Chemical Name Translation反式-茴香醚
Wiswesser Line Notation2U1R DO1 -T
LabNetwork Molecule IDLN00194700
InChIInChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
Canonical SMILESCOC1=CC=C(/C=C/C)C=C1
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分类

  • {SNA} Acyclic, Alkenes, Building B
  • {SNA} A-B, A-D, Alphabetical Listings, Certified Food Grade Products, Certified Natural Products, Flavors and Fragrances, Kosher Certified Products
  • {Chemicalbook} 食品添加剂: 食用香料(增香剂): 天然等同香料和人造香料
  • {SNA} A - D, A-B, Alphabetical Listings,

产品应用

  • 己烷雌酚、胆维他的中间体,生产茴香醛的原料。香料、药物制剂辅料等

相关文献及参考

  • [2]. Nakagawa Y, et al. Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells. Biochem Pharmacol. 2003 Jul 1;66(1):63-73.
  • [3]. Fahlbusch, et al. "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH.
  • Merck 14 ,643
  • Merck: 14,643
  • Merck: 14,643 Beilstein:6,566
  • Nakagawa, Y., and Suzuki, T., Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells. Biochem. Pharmacol. 66 , 63-73, (2003) 摘要
  • Short: II/27B
  • [1]. Tabanca N, et al. Estrogenic activity of isolated compounds and essential oils of Pim
  • [1]. Tabanca N, et al. Estrogenic activity of isolated compounds and essential oils of Pimpinella species from Turkey, evaluated using a recombinant yeast screen. Planta Med. 2004 Aug;70(8):728-35.

安全信息

GHS Symbol
WGK Germany2
Hazard Codes Xi,N Xi
Hazard statements
  • H411 Toxictoaquaticlifewithlonglastingeffects 对水生生物有毒性并具有长期影响。
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H227 Combustible liquid 可燃液体
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves
RTECSBZ9275000
Precautionary statements
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Warning
Safety Statements
  • S23 Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入气体/烟雾/蒸汽/喷雾;
  • S24 Avoid contact with skin 避免皮肤接触;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S37 Wear suitable gloves 戴适当手套;
  • 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;
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中,参考特别指示/安全收据说明书;
Risk Statements
  • R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
  • R51/53
Storage condition 2-8°C {LY} 2-8°C Light Sensitive {} {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 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 286 gm/kg/2Y-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Liver - tumors
   Skin and Appendages - tumors
REFERENCE :
   FCTOD7 Food and Chemical Toxicology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.20-    1982- Volume(issue)/page/year:
   27,11,1989

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 2090 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - coma
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            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - guinea pig
DOSE/DURATION           : 2167 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
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            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 900 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   THERAP Therapie.  (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris,
   France)  V.1-    1946-  Volume(issue)/page/year: 22,309,1967

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 650 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   THERAP Therapie.  (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris,
   France)  V.1-    1946-  Volume(issue)/page/year: 22,309,1967

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 3050 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (genera

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 200 ng/plate
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: AD-A116-715

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 10 umol/plate
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 60,143,1979

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 24 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 326,199,1995

TYPE OF TEST            : Morphological transformation
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 49 gm/kg
REFERENCE :
   FCTOD7 Food and Chemical Toxicology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.20-    1982- Volume(issue)/page/year:
   27,21,1989

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 800 mg/kg
SEX/DURATION            : female 1-10 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - pre-implantation mortality (e.g. reduction in
   number of implants per female; total number of implants per corpora lutea)
REFERENCE :
   IJPPAZ Indian Journal of Physiology and Pharmacology.  (All India Institute
   of Medical Sciences, Dept. of Physiology, Ansari Nagar, New Delhi 110 029,
   India)  V.1-    1957-  Volume(issue)/page/year: 39,63,1995

其他信息

  • 与乙醚、氯仿互溶,溶于苯、丙酮、乙酸乙酯、二硫化碳,不溶于水。
  • 茴香烯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 P0494 反-茴香脑 trans-Anethole 500G 868元 2014/06/02 P0494 反-茴香脑 trans-Anethole 25G 137元 2010/06/21 152531000 茴香烯 trans-Anethole 99% 100 ML 1545元
  • 含量分析:按气相色谱法(GT-10)测定。所用条件为: 柱长160cm,内径2mm,材质为玻璃。填料为聚乙二醇20M(Carbowax 20M),15%;载体为60/80目硅藻土(Chromosorlb W),85%。载气为氦,流量50ml/min。检测器用火焰电离型。 进样温度230℃。柱温等温段130℃/3min,温升速度3.5℃/min,终温等温于230℃。 顺式异构体先流出。最后按面积百分率计算含量(包括顺式异构体的百分率)。
  • 方法一:茴香脑在工业制法有多种,现介绍以下几种。(1)将茴香油或大茴香油冷却,析出结晶,经蒸馏并用酒精再结晶可得。也可以对茴香油精馏,收集230-234℃的馏了出物。或减压精馏,收集142℃(5.60kPa)或110℃(2.7kPa)馏分,即得茴香脑。(2)由对甲氧基苯基丁烯酸经220-240℃加热而得。(3)将对丙烯基苯甲醚与苛性碱一起加热,异构化为茴香脑。(4)由对丙烯基苯酚甲基化而得。(5)茴香醛与G2H5MgX作用,将生成物加热水脱水得到茴香脑。(6)茴香醛与丙酸酐及丙酸钠一起加热得到茴香脑。(7)在茴香醚和丙醛混合物中,于0℃加入浓盐酸和磷酸,使氯化氢气体达饱和,将产物与吡啶一起加热脱去氯化氢,即得到茴香脑。也可用氢溴酸代替浓盐酸,产物用金属钠处理,脱溴化氢即得到茴香脑。(8)将对溴茴香醚制备成Grignard试剂,并与烯丙基溴反应,生成对甲氧基苯丙烯,然后与氢氧化钾一起加热,异构化得到茴香脑。
  • 使用限量:FEMA(mg/kg):软饮料11;冷饮2溷糖果340;焙烤食品150;
  • 方法一:由大茴香脑含量高的精油(如茴香油)单离。 由对甲酚和甲醛反应后再与乙醛缩合而成。
  • 急救治疗:制剂:误服者应立即催吐,洗胃。吸入中毒者可用半胱氨酸衍生物,如甲基胱氨酸给病人进行15分钟雾化吸入。神经系
  • Sigma Aldrich:4180-23-8(sigmaaldrich)
  • 参考质量标准:FCC,1996
  • {Chemical
  • 图谱信息:茴香烯(4180-23-8)核磁图( 1 HNMR) 茴香烯(4180-23-8)红外图谱(IR1) 茴香烯(4180-23-8)Raman光谱 茴香烯(4180-23-8)红外图谱(IR2) 茴香烯(4180-23-8)核磁图( 13 CNMR) 茴香烯(4180-23-8)质谱(
  • 上游原料:茴香脑 --> 小茴香油
  • 中毒症状:制剂:可表现为恶心、呕吐、呼吸困难、急促,血压过低、脉搏迟缓,接着出现高血压和心博过快,也可能短时期反应迟钝。然后全身兴奋,严重时有惊厥等现象或症状。
  • Sigma Aldrich:104-46-1(sigmaaldrich)
  • 参考质量标准:FCC,1996 含量 ≥99.0%(W/W) 醇中溶解度(OT-43) lml溶于2mL 96%乙醇 旋光度 ≤-0.15°~+0.15° 馏程 231~237℃ 酚类试验 正常 凝固点 ≥20℃ 折射率(
  • FEMA:2086
  • 用途三:主要用于提取茴香脑,也用于配制饮料、食品、烟草等的增香剂以及医药方面。
  • 下游产品:对甲氧基苯甲醛 --> 茴三硫 --> 茴香烯 --> 4,4'-(1,2-二乙基亚乙基)二苯酚 --> 1-甲氧-4丙基苯
  • 上游原料:氢氧化钠 --> 钠 --> 苯甲醚 --> 对甲氧基苯甲醛 --> 3-溴丙烯 --> 丙酸酐 --> 二甲醚 --> 对苯二甲醚 --> 丙酸钠 --> 巴豆酸 --> 4-溴苯甲醚 --> 4-苯基-1-丁烯 --> 烯丙苯 --> 4-烯丙基苯甲醚 --> 小茴香油 --> 大茴香油

系列性分类


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