CAS 331-39-5 MFCD00004392-3,4-Dihydroxycinnamic Acid 咖啡酸 TAO{mole}

3,4-Dihydroxycinnamic Acid 咖啡酸

CAS 331-39-5 MFCD00004392

化学结构图

SMILES: O=C(O)/C=C/c1ccc(O)c(O)c1

化学属性

Mol. Formula	C9H8O4
Mol. Weight	180
Melting Point	194-198
Density	1.478
TSCA	No
Solubility	溶于热水
Stability	对湿度敏感
Appearance	黄色结晶。溶于热水及乙醇。 powder

别名和识别编码

Chemical Name	3,4-Dihydroxycinnamic Acid
CAS Number	331-39-5
Synonym	(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)- 3,4-Dihydroxybenzeneacrylic acid 3,4-Dihydroxycinnamic acid 3,4-dihydroxy-cinnamicaci 3,4-二羟基肉桂酸(咖啡酸)/CAFFEIC ACID 3,4-二羟基苯乙烯酸 3,4-二羥桂皮酸 3-(3,4-Dihydroxyphenyl)-2-propenoic acid 3-(3,4-Dihydroxyphenyl)propenoic acid 3-(3,4-dihydroxyphenyl)-2-propenoicaci 4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene Caffeic acid Caffeicacid,96% 咖啡酸
PubChem Substance ID	689043
EC Number	206-361-2
Beilstein Registry Number	1954563
MDL Number	MFCD00004392
Reaxys-RN	1954563
Merck Number	1635
Chemical Name Translation	咖啡酸
Wiswesser Line Notation	QV1U1R CQ DQ
InChIKey	QAIPRVGONGVQAS-DUXPYHPUSA-N
LabNetwork Molecule ID	LN00222697
InChI	InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+

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产品应用

一种天然的存在于植物中的酚酸化合物，是一种抗氧剂，抑制白三烯（leukotrienes）的合成（白三烯涉及到免疫、发炎和敏感症的调控），抑制 Cu2+-诱导的 LDL的氧化。

安全信息

GHS Symbol

WGK Germany3

Hazard statements

H315 Causes skin irritation 会刺激皮肤
H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
H351 Suspected of causing cancer 怀疑致癌
H319 Causes serious eye irritation 严重刺激眼睛
H335 May cause respiratory irritation 可能导致呼吸道刺激

Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Hazard Codes Xn Xn,Xi

RTECSGD8950000

Precautionary statements

P201 Obtain special instructions before use. 使用前获取专门指示。
P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
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。
P281 Use personal protective equipment as required. 使用所需的个人防护装备。
P302+P350
P302+P352
P302+P352+P332+P313+P362+P364
P305+P351+P338
P308+P313
P332+P313
P337+P313
P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
P501 Dispose of contents/container to..… 处理内容物/容器.....

Signal word Warning

Safety Statements

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

R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用

Storage condition Store at RT. 密封保存。

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1613 gm/kg/96W-C
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Kidney, Ureter, Bladder - Kidney tumors
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   51,5655,1991

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 728 gm/kg/2Y-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Gastrointestinal - tumors
   Kidney, Ureter, Bladder - Kidney tumors
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   51,5655,1991

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >721 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: 104,793,1984

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1959-  Volume(issue)/page/year:
   36,227,1976

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 200 mg/L
REFERENCE :
   CALEDQ Cancer Letters (Shannon, Ireland).  (Elsevier Scientific Pub. Ireland
   Ltd., POB 85, Limerick, Ireland)  V.1-    1975- Volume(issue)/page/year:
   14,251,1981

TYPE OF TEST            : Gene conversion and mitotic recombination
TEST SYSTEM             : Yeast - Saccharomyces cerevisiae
DOSE/DURATION           : 300 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 135,109,1984

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 307 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 204,219,1988

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 480 mg/kg
SEX/DURATION            : female 5-12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1959-  Volume(issue)/page/year:
   36,227,1976

其他信息

咖啡酸价格(试剂级):更新日期产品编号产品名称包装价格 2014/06/02 C0002 咖啡酸 Caffeic Acid 5G 235元 2014/06/02 C0002 咖啡酸 Caffeic Acid 25G 986元 2010/06/21 114930250 咖啡酸 3,4-Dihydroxycinnamic acid 99+%, predominantly trans isomer 25 GR 1538元
MSDS 信息:Caffeic acid(331-39-5).msds
HPLC法测定蒲公英中咖啡酸的含量:[供试品] 菊科植物蒲公英Taraxacum mongolicum Hand. Mazz.，碱地蒲公英T. sinicum Kitag。 (1) 色谱条件：用十八烷基硅烷键含硅胶为填充剂；甲醇-磷酸盐缓冲液(磷酸二氢钠1.56g，加水使溶解成1000ml，再加1%磷酸溶液调节pH值至3.8～4.0，即得) (23：77)为流动相；检测波长为323nm；柱温40℃。理论板数按咖啡酸峰计算，不低于3000。 (2) 对照品溶液的配制：取咖啡酸对照品7.5mg，精密称定，置50ml量瓶中，加甲醇至刻度，摇匀；精密量取2ml，置10ml量瓶中，加甲醇至刻度，摇匀，即得(
储运特性:库房通风低温干燥
提取方法:咖啡酸为常见酚酸类化合物，有提升白细胞的作用，易与咖啡碱混淆。在植物界中普遍存在，主要来源于柠檬果皮、毛莨科植物升麻根茎、缬草根等多种植物。咖啡酸与阿魏酸、芥子酸、对羟基桂皮酸是在植物中几乎普遍存在羟基桂皮酸，此类产品分子结构的侧链上有共轭双键，在紫外光下显荧光，多数呈蓝色荧光。这是纸色谱或薄层色谱检查的有利条件。提取方法：单穗升麻根茎用甲醇提取，减压浓缩去甲醇。残留物加热水使溶，趁热滤除不溶物。冷却后加苯萃取，苯溶液用1%碳酸氢钠水溶液洗涤，收集洗涤液。加稀盐酸酸化，用苯再从中游离出的有机酸，减压浓缩去苯，残留物为咖啡酸富集制品。
毒性分级:中毒
Alfa Aesar:3,4-二羟基苯乙烯酸,99% 3,4-Dihydroxycinnamic acid, predomina
可燃性危险特性:热分解辛辣刺激烟雾
HPLC法测定蒲公英中咖啡酸的含量:[供试品] 菊科植物蒲公英Taraxacum mongolicum Hand. Mazz.，碱地蒲公英T. sinicum Kitag。 (1) 色谱条件：用十八烷基硅烷键含硅胶为填充剂；甲醇-磷酸盐缓冲液(磷酸二氢钠1.56g，加水使溶解成1000ml，再加1%磷酸溶液调节pH值至3.8～4.0，即得) (23：77)为流动相；检测波长为323nm；柱温40℃。理论板数按咖啡酸峰计算，不低于3000。 (2) 对照品溶液的配制：取咖啡酸对照品7.5mg，精密称定，置50ml量瓶中，加甲醇至刻度，摇匀；精密
Sigma Aldrich:331-39-5(sigmaaldrich)
Acros Organics:3，4-二羟基肉桂酸/ 咖啡酸 3,4-Dihydroxycinnamic acid, predominantly trans isomer, 99+%(331-39-5)
升白细胞药:咖啡酸也是一种止血升白细胞药，具有收缩凝固微血管、提高凝血因子功能、升高白细胞和血小板的作用。适用于外科手术时预防出血或止血，以及内科、妇产科等出血性疾病的止血。也用于各种原因引起的白细胞减少症、血小板减少症。
Hazard Note:Irritant
图谱信息:咖啡酸(331-39-5)红外图谱(IR2) 咖啡酸(331-39-5)质谱(MS) 咖啡酸(331-39-5)红外图谱(IR1) 咖啡酸(331-39-5)核磁图( 1 HNMR)
易溶于热水、冷乙醇，微溶于冷水。碱溶液从黄色变成橙色。194℃软化，223～225℃分解。有刺激性。有致癌可能性。
{Chemi
急性毒性:腹腔-大鼠 LDL0: 1500 毫克/公斤
MOL 文件:331-39-5.mol
用途二:咖啡酸的中间体。用于有机合成。