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原儿茶醛; 原二茶醛; 茶酚甲醛; 茶醛; 3,4-二羟基苯甲醛

用途

Protocatechualdehyde (Catechaldehyde) 是从 Salviae Miltiorrhizae 中分离出来的一种天然多酚化合物,具有多种生物活性,可作为抗氧化、抗衰老、抗菌消炎剂被广泛应用于多个医学领域。

名称

[ CAS 号 ]:
139-85-5

[ 中文名 ]:
3,4-二羟基苯甲醛

[ 英文名 ]:
3,4-Dihydroxybenzaldehyde

[中文别名 ]:

[英文别名 ]:

Benzaldehyde, 3,4-dihydroxy-
1,2-dihydroxy-4-formylbenzene
3,4-Dihydroxy benzaldehyde
4-formyl-1,2-benzenediol
3,4-Dihydroxybenzyl aldehyde
RANCINAMYCIN IV
MFCD00003370
UNII-4PVP2HCH4T
4-formyl-1,2-dihydroxybenzene
EINECS 205-377-7

生物活性

[ 描述 ]:

[ 相关类别 ]:

研究领域 >> 癌症

研究领域 >> 感染

信号通路 >> 其他 >> 其他

[体外研究]

原儿茶醛(PCA)(50,100μM,24/48小时)处理的MCF-7细胞在24小时内显着降低细胞生长11％和20％,在48小时内分别降低22％和27％[2]。在50μM和100μM的浓度下,原儿茶醛(50,100μM,24小时)处理的MCF-7细胞分别增加1.9倍和2.6倍。 PCA抑制雌激素受体(ER)阳性(MCF-7)乳腺癌细胞的增殖,但不抑制ER阴性(MDA-MB-231)乳腺癌细胞的增殖[2]。原儿茶醛(0,100,200μM,HCT116和SW480细胞中48小时)影响HDAC的酶活性,并观察到PCA处理以剂量依赖性方式导致HDAC活性的抑制[3]。细胞增殖测定[2]细胞系：人乳腺癌细胞(MCF-7和MDA-MB-231)浓度：0,5,10,25,50和100μM孵育时间：24,48小时结果：抑制MCF -7细胞生长。细胞凋亡分析[2]细胞系：人乳腺癌细胞(MCF-7和MDA-MB-231)浓度：0,5,10,25,50和100μM孵育时间：24,48小时结果：细胞凋亡增加MCF-7细胞。

[参考文献]

[1]. Li S, et al. Evaluation of the Antibacterial Effects and Mechanism of Action of Protocatechualdehyde against Ralstonia solanacearum. Molecules. 2016 Jun 9;21(6).

[2]. Choi J, et al. Anticancer activity of protocatechualdehyde in human breast cancer cells. J Med Food. 2014 Aug;17(8):842-8.

[3]. Jeong JB, et al. Protocatechualdehyde possesses anti-cancer activity through downregulating cyclin D1 and HDAC2 in human colorectal cancer cells. Biochem Biophys Res Commun. 2013 Jan 4;430(1):381-6.

物理化学性质

[ 密度 ]:
1.4±0.1 g/cm3

[ 沸点 ]:
295.4±20.0 °C at 760 mmHg

[ 熔点 ]:
150-157 °C(lit.)

[ 分子式 ]:
C₇H₆O₃

[ 分子量 ]:
138.12

[ 闪点 ]:
146.7±18.3 °C

[ 精确质量 ]:
138.031693

[ PSA ]:
57.53000

[ LogP ]:
1.14

[ 外观性状 ]:
棕色粉末

[ 蒸汽压 ]:
0.0±0.6 mmHg at 25°C

[ 折射率 ]:
1.674

[ 储存条件 ]:
2-8°C

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

[ 水溶解性 ]:
50 g/L (20 ºC)

MSDS

详细MSDS(安全技术说明书)

毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UL0380000

CHEMICAL NAME :: Protocatechualdehyde

CAS REGISTRY NUMBER :: 139-85-5

LAST UPDATED :: 198311

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C7-H6-O3

MOLECULAR WEIGHT :: 138.13

WISWESSER LINE NOTATION :: VHR CQ DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 205 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: APFRAD Annales Pharmaceutiques Francaises. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1943- Volume(issue)/page/year: 15,461,1957

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56 mg/kg

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

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#07875

安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H315-H319-H335

[ 警示性声明 ]:
P261-P305 + P351 + P338

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xi:Irritant

[ 风险声明 (欧洲) ]:
R36/37/38

[ 安全声明 (欧洲) ]:
S26-S36-S37/39

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
3

[ RTECS号 ]:
UL0380000

[ 海关编码 ]:
29124900

合成路线

详细合成路线

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制备

1.由3,4-亚甲基二氧基苯甲醛经下列步骤制得。将新处理过的五氯化磷分次加入3,4-亚甲基二氧基苯甲醛中，开始时反应很剧烈，需用冰水冷却，同时应防止湿气侵入。大约在加入一半五氯化磷后应变慢，可不再冷却。五氯化磷的用量为3,4-亚甲基二氧基苯甲醛的3倍（摩尔）。将所得反应液慢慢加热1h，放出氯化氢，再减压抽出挥发物。然后，将反应物倾入冷水中，析出的乳状油层放置固化。再慢慢沸腾3h，加活性炭过滤，滤液减压浓缩，冷却至0℃，析出结晶。过滤、水洗后用水重结晶，得成品。

2. 烟草：OR，26；FC，54。

海关

[ 海关编码 ]: 2912499000

[ 中文概述 ]:
2912499000. 其他醛醚、醛酚及含其他含氧基的醛. 增值税率:17.0%. 退税率:9.0%. 监管条件:无. 最惠国关税:5.5%. 普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 四聚甲醛报明外观

[ Summary ]:
2912499000. other aldehyde-ethers, aldehyde-phenols and aldehydes with other oxygen function. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:5.5%. General tariff:30.0%

文献

Synthesis and accumulation of aromatic aldehydes in an engineered strain of Escherichia coli.

J. Am. Chem. Soc. 136(33) , 11644-54, (2014)

Aromatic aldehydes are useful in numerous applications, especially as flavors, fragrances, and pharmaceutical precursors. However, microbial synthesis of aldehydes is hindered by rapid, endogenous, an...

3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors.

Bioorg. Med. Chem. 15 , 2006-15, (2007)

Phenoloxidase (PO), also known as tyrosinase, is a key enzyme in insect development, responsible for catalyzing the hydroxylation of tyrosine into o-diphenols and the oxidation of o-diphenols into o-q...

Chromatographic evaluation and QSAR optimization for benzoic acid analogues against carbonic anhydrase III.

J. Enzyme Inhib. Med. Chem. 30 , 420-9, (2015)

An HPLC-size exclusion method was developed as an assay method to evaluate the binding of tested compounds with carbonic anhydrase III (CAIII) enzyme. Inhibition of CAIII by a group of benzoic acid an...

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