丁香酚

丁香酚用途

【用途一】
用于配制康乃馨型香精及制异丁香酚和香兰素等，也用作杀虫剂和防腐剂
【用途二】
丁香酚是我国规定允许使用的食用香料，主要用于配制薄荷、坚果、辛香型食品香精和烟用香精，用量按正常生产需要，在肉类中使用量为40~2000mg/kg；胶姆糖中500mg/kg；调味品中9.6～100mg/kg；烘烤食品中33mg/kg；糖果中32mg/kg；冷饮中3.1mg/kg；软饮料中1.4mg/kg；布丁类中0.6mg/kg。此外，丁香酚具有防腐作用和很强的杀菌力。
【用途三】
是调配香石竹花香的体香。广泛用于香薇等香型，可作为修饰剂和定香剂，用入有色香皂加香。可用于许多花香香精如玫瑰等。也可用于辛香、木香和东方型、薰香型中，还可用于食用的辛香型、薄荷、坚果、各种果香、枣子香等香精及烟草香精中。
【用途四】
GB 2760—96规定为允许使用的食用香料。主要用于配制烟熏火腿、坚果和香辛料等型香精。亦为合成香兰素的主要原料。
【用途五】
丁子香酚具有浓郁的石竹麝香气味，是康及謦系香精的调合基础，在化妆、皂用、食用等香精的调合中均有使用。丁子香酚具有很强的杀菌力，作为局部镇痛药可用于龋齿，且兼有局部防腐作用。丁子香酚是其他一些香料的中间体，衍生物有异丁子香酚、甲基丁子香酚、甲基异丁子香酚、乙酰丁子香酚、乙酰导师丁香酚、苄基异丁子香酚等。丁子香酚在氢氧化钾中加热时，丙烯基的双键发生重排作用，变为与苯环共轭的α-丙烯基，从而得到异丁香酚，经乙酰化和温和的氧化，α-丙烯基断裂，即得香草醛，它是一种重要的人造调味剂的主要成分。丁子香酚还可用于制造治疗肺结核的特效药异烟肼。

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丁香酚名称

[ CAS 号 ]:
97-53-0

[ 中文名 ]:
丁香酚

[ 英文名 ]:
Eugenol

[中文别名 ]:

[英文别名 ]:

4-Allyl-2-methoxyphenol
Eugenic acid
p-Allylguaiacol
2-methoxy-4-allyl phenol
2-methoxy-4-(prop-2-en-1-yl)phenol
Eugenol
2U1R DQ CO1
4-allylguaiacol
2-methoxy-4-(2-propen-1-yl)phenol
p-Eugenol

丁香酚生物活性

[ 描述 ]:

Eugenol是丁香中发现的精油,具有抗菌,驱虫和抗氧化活性。 Eugenol也可抑制脂质过氧化。

[ 相关类别 ]:

信号通路 >> 抗感染 >> 细菌

信号通路 >> 抗感染 >> 寄生物

天然产物 >> 酚类

研究领域 >> 炎症/免疫

研究领域 >> 感染

[ 靶点 ]

Bacterial, Parasite[1]

[体外研究]

O. gratissimum的精油以及丁香酚可有效抑制捻转血矛线虫卵的易蚀性,显示出可用于治疗小反刍动物的胃肠蠕虫病。浓度为0.50％时,精油和丁香酚显示出最大的抑制作用[1]。丁香酚抑制黄嘌呤-黄嘌呤氧化酶系统中超氧阴离子的产生,浓度为250μM时,其浓度为50％。丁子香酚还抑制羟基自由基的产生达70％。通过水杨酸盐羟基化为2,3-二羟基苯甲酸酯测得的OH-自由基形成被依普利诺在250μM时抑制到46％[2]。丁香酚除了抗氧化作用外,还通过调节HPA轴和脑单胺能通路来保护RS诱导的IBS样胃肠功能障碍的发展。丁香酚(50mg/kg)减少80％的RS诱导的粪便颗粒增加,类似于恩丹西酮。丁子香酚减弱80％的应激诱导的血浆皮质酮增加,并调节PFC和杏仁核中的5-羟色胺能系统。丁香酚减弱应激诱导的去甲肾上腺素的变化,并增强所有大脑区域的抗氧化防御系统[3]。

[体内研究]

口服施用丁子香酚(33mg/kg)2天引起膝关节水肿的显着抑制,其在治疗结束时继续显着降低。 2天后,丁香酚处理的分枝杆菌性关节炎大鼠的爪肿胀明显减少[4]。

[细胞实验]

精油和丁香酚在Tween 20（0.5％）水溶液中稀释，浓度如下：0.0625,0.12,0.25,0.5和1.0％，用于卵孵化试验[1]。

[动物实验]

大鼠：关节炎大鼠的治疗组在诱导关节炎前1天口服给予英维多（0.33mL / kg或33mg / kg）或丁子香酚（0.33mL / kg或33mg / kg）。该治疗每天持续26天。 Mycobaterium trated大鼠口服生理盐水[4]。

[参考文献]

[1]. Pessoa LM, et al. Anthelmintic activity of essential oil of Ocimum gratissimum Linn. and eugenol against Haemonchus contortus. Vet Parasitol. 2002 Oct 16;109(1-2):59-63.

[2]. Reddy AC, et al. Studies on the inhibitory effects of curcumin and eugenol on the formation of reactive oxygenspecies and the oxidation of ferrous iron. Mol Cell Biochem. 1994 Aug 17;137(1):1-8.

[3]. Garabadu D, et al. Protective effect of eugenol against restraint stress-induced gastrointestinal dysfunction: Potential use in irritable bowel syndrome. Pharm Biol. 2015 Jul;53(7):968-74.

[4]. Sharma JN, et al. Suppressive effects of eugenol and ginger oil on arthritic rats. Pharmacology. 1994 Nov;49(5):314-8.

[相关活性小分子]

丁香酚物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
255.0±0.0 °C at 760 mmHg

[ 熔点 ]:
−12-−10 °C(lit.)

[ 分子式 ]:
C₁₀H₁₂O₂

[ 分子量 ]:
164.201

[ 闪点 ]:
119.8±8.1 °C

[ 精确质量 ]:
164.083725

[ PSA ]:
29.46000

[ LogP ]:
2.20

[ 外观性状 ]:
无色至淡的黄色液体带有一种强烈的丁香的气味

[ 蒸汽压 ]:
0.0±0.5 mmHg at 25°C

[ 折射率 ]:
1.536

[ 储存条件 ]:
库房通风低温干燥,与食品原料分开储运

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

[ 水溶解性 ]:
slightly soluble

丁香酚MSDS

详细MSDS(安全技术说明书)

丁香酚毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SJ4375000

CHEMICAL NAME :: Phenol, 4-allyl-2-methoxy-

CAS REGISTRY NUMBER :: 97-53-0

BEILSTEIN REFERENCE NO. :: 1366759

LAST UPDATED :: 199701

DATA ITEMS CITED :: 44

MOLECULAR FORMULA :: C10-H12-O2

MOLECULAR WEIGHT :: 164.22

WISWESSER LINE NOTATION :: 1U2R DQ CO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Human

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Human - man

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Mammal - pig

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - guinea pig

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1930 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - coma Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LC - Lethal concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2580 mg/m3/4H

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 800 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness Kidney, Ureter, Bladder - other changes

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness Kidney, Ureter, Bladder - other changes

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

ROUTE OF EXPOSURE :: Intratracheal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 11 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - structural or functional change in trachea or bronchi Lungs, Thorax, or Respiration - acute pulmonary edema Lungs, Thorax, or Respiration - chronic pulmonary edema

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

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

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 72 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Gastrointestinal - nausea or vomiting

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 2130 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

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

ROUTE OF EXPOSURE :: Intratracheal

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 17 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - structural or functional change in trachea or bronchi Lungs, Thorax, or Respiration - acute pulmonary edema Lungs, Thorax, or Respiration - chronic pulmonary edema

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 68 gm/kg/34D-I

TOXIC EFFECTS :: Liver - other changes Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 70 gm/kg/14D-C

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 84 gm/kg/14D-C

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 37080 mg/kg/2Y-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - hamster Embryo

DOSE/DURATION :: 300 ppb

REFERENCE :: SHIGAZ Shigaku. Ondotology. (Nippon Shika Daigaku Shigakkai, 1-9-20 Fujimi, Chiyodaku, Tokyo 102, Japan) V.38- 1949- Volume(issue)/page/year: 74,1365,1987 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 36,75,1985 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 13,545,1975 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 82100 No. of Facilities: 1034 (estimated) No. of Industries: 17 No. of Occupations: 31 No. of Employees: 37569 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 82100 No. of Facilities: 9995 (estimated) No. of Industries: 82 No. of Occupations: 91 No. of Employees: 187937 (estimated) No. of Female Employees: 83766 (estimated)

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丁香酚安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H317-H319

[ 警示性声明 ]:
P280-P305 + P351 + P338

[ 个人防护装备 ]:
Faceshields;full-face respirator (US);Gloves;Goggles;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ 危害码 (欧洲) ]:
Xn:Harmful;

[ 风险声明 (欧洲) ]:
R22;R38

[ 安全声明 (欧洲) ]:
S26-S36-S24/25

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

[ WGK德国 ]:
1

[ RTECS号 ]:
SJ4375000

[ 海关编码 ]:
29095090

丁香酚合成路线

详细合成路线

丁香酚上下游产品

丁香酚上游产品

丁香酚下游产品

丁香酚制备

【方法一】
用丁香油之类含有大量丁香酚的精油，加30%氢氧化钠液处理，再加无机酸或通人二氧化碳气使之析出。或使之与醋酸钠加成，以使游离出来后再经水蒸气蒸馏而得纯品。
【方法二】
丁香酚天然存在于多种精油中，尤以丁香油(含80%)、月桂叶油(含80%)、丁香罗勒油(含60%)含量为最多，在樟脑油、金合欢油、紫罗兰油、依兰油中均有存在。工业上可以从天然精油中单离，也可由化学合成而得。但化学合成法产生的同分异构体，沸点非常接近而分离极为困难，目前以单离法为主。
天然精油单离法
以多年生亚灌木丁香罗勒为原料，经水蒸气蒸馏得精油和水的混合物。油水混合物中加入20%的氢氧化钠，再进行水蒸气蒸馏除去非酸性物质。在50℃下将所得丁香酚钠溶液加入30%的硫酸搅拌中和至Ph=2～3(水层)。静置后分出下层粗丁香油，经减压蒸馏得丁香酚成品。
化学合成法
将烯丙基溴、邻甲氧基苯酚、无水丙酮和无水碳酸钾加入反应釜中，加热回流数小时。冷却后加水稀释，然后用乙醚提取。提取物用10%的氢氧化钠洗涤，再用无水碳酸钾干燥。常压蒸馏回收乙醚、丙酮后进行减压蒸馏，收集110~113℃(1600Pa)的馏分，即为邻甲氧基苯基烯丙醚。将其煮沸回流1h后冷却，所得油状物用乙醚溶解，再用Lo%的氢氧化钠溶液提取，提取液经盐酸酸化后乙醚萃取。萃取液用无水硫酸钠干燥，常压蒸馏回收乙醚后即得丁香粉成品。也可由邻甲氧基苯酚与烯丙基氯在金属铜的催化和100℃下一步反应得到成品。
【方法三】
丁子香酚主要存在于丁香罗勒（Oci-mum gratissimum L）的油内及樟属肉桂叶的油内，是多种芳香油的成分，其中尤以丁香油、桂叶油、罗勒油、月桂油含量最多。丁子香酚尽管也可用合成的方法制备，但工业上一般都从植物或芳香油中分离萃出。可采用丁香罗勒为原料，丁香罗勒原产于塞舌尔、科摩罗。1965年从前苏联引入我国。在长江流域以南作为多处生亚灌本栽培。花穗中丁香罗勒油含量最高，叶次之，茎杆更次之。油中的主要成分是丁子香酚。占60-70%，尚有芳樟醇、对伞花素、罗勒烯等。合成法丁子香酚，由邻甲氧基苯酚与溴丙烯反应，再经加热重排而得。

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丁香酚海关

[ 海关编码 ]: 2909500000

[ 中文概述 ]:
2909500000. 醚酚、醚醇酚及其卤化、磺化、硝化或亚硝化衍生物. 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

[ Summary ]:
2909500000 ether-phenols, ether-alcohol-phenols and their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

丁香酚文献

Can Ocimum basilicum L. and Ocimum tenuiflorum L. in vitro culture be a potential source of secondary metabolites?

Food Chem. 194 , 55-60, (2015)

In this study Ocimum basilicum L. (OB) and Ocimum tenuiflorum L. (OT) in vitro culture standardisation for increasing eugenol distribution, in comparison to their respective field grown parts was carr...

Volatile Compounds from Grape Skin, Juice and Wine from Five Interspecific Hybrid Grape Cultivars Grown in Québec (Canada) for Wine Production.

Molecules 20 , 10980-1016, (2015)

Developed from crosses between Vitis vinifera and North American Vitis species, interspecific hybrid grape varieties are becoming economically significant in northern areas, where they are now extensi...

Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay.

Bioorg. Med. Chem. Lett. 20 , 2111-4, (2010)

The effect of essential oils, such as raspberry ketone, on androgen (AR) receptor was investigated using a MDA-kb2 human breast cancer cell line for predicting potential AR activity. Among them, eugen...

更多文献

丁香酚

丁香酚用途

丁香酚名称

丁香酚生物活性

丁香酚物理化学性质

丁香酚MSDS

详细MSDS(安全技术说明书)

丁香酚毒性和生态

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

丁香酚安全信息

丁香酚合成路线

详细合成路线

丁香酚上下游产品

丁香酚上游产品

丁香酚下游产品

丁香酚制备

丁香酚海关

丁香酚文献

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