(±)-樟脑(合成)

(±)-樟脑(合成)用途

【用途一】
广泛用于医药、塑料工业及日常生活中防虫、防蛀、防臭
【用途二】
用于制药工业及赖氏法测定分子量，也用作杀虫剂
【用途三】
是重要的药品和化工基础原料，可用作增塑剂，用于生产塑料、假象牙、清漆、炸药、驱虫剂、防腐剂等
【用途四】
用作医药中间体
【用途五】
用于生产赛璐珞、胶片、人造象牙、香精等，也用于生产橡胶、电绝缘材料、飞机零件等；还可作为军火工业制无烟火药的爆炸稳定剂，农药工业制杀虫剂，医药工业配制的兴奋剂、强心剂、十滴水、清凉剂、止痒剂及衣服、书籍的防蛀药、防腐剂等。
【用途六】
微量分析和气相色谱参比样品。纤维素酯和醚的增塑剂，炸药，烟火，杀虫剂，制造赛璐珞。溶解度：25℃时1g溶于1ml乙醇、1ml乙醚、0.5ml氯仿、0.4ml丙酮、1.5ml松节油、0.5ml冰乙酸和约800ml水中。溶于苯胺、硝基苯、二硫化碳、1,2,3,4-四氢化萘、萘烷、甲基环己醇、石油醚、高碳醇、挥发油、不挥发油、浓无机酸、苯酚、氨水和液体二氧化硫。

(±)-樟脑(合成)名称

[ CAS 号 ]:
76-22-2

[ 中文名 ]:
樟脑

[ 英文名 ]:
(+/-)-Camphor

[中文别名 ]:

2-莰酮

[英文别名 ]:

(+)-bornan-2-one
Bicyclo(2.2.1)heptan-2-one, 1,7,7-trimethyl-
camphanone
3-Fluor-2,2-dimethyl-bicyclo<2.2.1>heptan
(1S,4S)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one
1,7,7-Trimethylbicyclo[2.2.1]-2-heptanone
2-Kamfanon
D-CAMPHOR
(±)-bornan-2-one
2-Oxo-bornan

(±)-樟脑(合成)生物活性

[ 描述 ]:

Camphor ((±)-Camphor) 是一种外用抗感染和抗瘙痒剂,口服有驱风作用。然而,Camphor 摄入时有毒。Camphor 具有抗病毒,镇咳和抗癌活性[1]。Camphor 是一种 TRPV3 激动剂[2]。

[ 相关类别 ]:

信号通路 >> 跨膜转运 >> TRP频道

天然产物 >> 萜类化合物和糖苷

研究领域 >> 癌症

研究领域 >> 炎症/免疫

研究领域 >> 感染

[ 靶点 ]

TRPV3[2]

[体外研究]

樟脑通过PI3K/AKT和ERK信号传导途径诱导成纤维细胞增殖。 MTT测定结果显示,与0μMCamphor处理相比,32.5,65,130和260μM樟脑的成纤维细胞活力分别增加至108.9±6.6％,118.6±2.8％,127.7±4.2％和131.6±7.2％。樟脑处理24小时后,ROS的产生量增加了17.97％,而未处理对照组为5.04％[3]。

[细胞实验]

将原代真皮成纤维细胞（2×10 4个细胞/ mL）细胞接种在96孔板中的200μL含有10％FBS的培养基中。 24小时后，用各种浓度的洋甘菊水溶胶或樟脑（0-260μM）处理细胞。处理后，向每个孔中加入20μLMTT溶液（5mg / mL），然后在潮湿环境中孵育3-4小时。除去上清液并加入150μLDMSO。细胞活力由570nm处的吸光度确定，使用Sunrise酶标仪测量[3]。

[参考文献]

[1]. Chen W, et al. Camphor--a fumigant during the Black Death and a coveted fragrant wood in ancient Egypt and Babylon--a review. Molecules. 2013 May 10;18(5):5434-54.

[2]. Billen B, et al. Different ligands of the TRPV3 cation channel cause distinct conformational changes as revealedby intrinsic tryptophan fluorescence quenching. J Biol Chem. 2015 May 15;290(20):12964-74.

[3]. Tran TA, et al. Camphor Induces Proliferative and Anti-senescence Activities in Human Primary Dermal Fibroblasts and Inhibits UV-Induced Wrinkle Formation in Mouse Skin. Phytother Res. 2015 Dec;29(12):1917-25.

[相关活性小分子]

辣椒碱 | 辣椒平 | 5-(N-乙基-N-异丙基)阿米洛利 | 氯化二亚苯基碘鎓 | 2-(1,3-二甲基-2,6-二氧代-2,3-二氢-1H-嘌呤-7(6H)-基)-N-(4-异丙基苯基)乙酰胺 | 1-[2-(4-甲氧基)-2-[3-(4-甲氧基苯基)丙氧基]乙基]咪唑 | HC-067047 | AMG9810 | GSK1016790A | SAR7334 | PF-4840154 | RN-1734 | AMG 517 | 3-(4-氯苯基)-N-(3-甲氧基苯基)-2-丙烯酰胺 | 冰素

(±)-樟脑(合成)物理化学性质

[ 密度 ]:
1.0±0.1 g/cm3

[ 沸点 ]:
207.4±0.0 °C at 760 mmHg

[ 熔点 ]:
175-177 °C(lit.)

[ 分子式 ]:
C₁₀H₁₆O

[ 分子量 ]:
152.233

[ 闪点 ]:
64.4±0.0 °C

[ 精确质量 ]:
152.120117

[ PSA ]:
17.07000

[ LogP ]:
2.13

[ 外观性状 ]:
无色或白色的结晶粉末,带有一种强烈的像樟脑丸的气味

[ 蒸汽密度 ]:
5.2 (vs air)

[ 蒸汽压 ]:
0.2±0.4 mmHg at 25°C

[ 折射率 ]:
1.485

[ 储存条件 ]:
库房通风低温干燥,与氧化剂、酸类分开存放

[ 稳定性 ]:
Stable. Combustible. Incompatible with strong oxidizing agents, metallic salts, combustible materials, organics.

[ 水溶解性 ]:
0.12 g/100 mL (25 ºC)

(±)-樟脑(合成)MSDS

详细MSDS(安全技术说明书)

(±)-樟脑(合成)毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EX1225000

CHEMICAL NAME :: Camphor

CAS REGISTRY NUMBER :: 76-22-2

BEILSTEIN REFERENCE NO. :: 3196099

LAST UPDATED :: 199712

DATA ITEMS CITED :: 50

MOLECULAR FORMULA :: C10-H16-O

MOLECULAR WEIGHT :: 152.26

WISWESSER LINE NOTATION :: L55 A CVTJ A1 A1 B1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - infant

DOSE/DURATION :: 70 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - convulsions or effect on seizure threshold Gastrointestinal - changes in structure or function of salivary glands

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 51 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 100 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 29 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 900 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 70 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 :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1310 mg/kg

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

TYPE OF TEST :: LCLo - Lowest published lethal concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/m3/3H

TOXIC EFFECTS :: Behavioral - muscle contraction or spasticity

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Behavioral - rigidity (including catalepsy)

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Behavioral - excitement

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 800 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 400 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Behavioral - rigidity (including catalepsy)

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 240 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 210 mg/m3/3H/7W-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - emphysema

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 33 mg/m3/3H/7W-I

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes Cardiac - other changes Lungs, Thorax, or Respiration - emphysema

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 224,157,1989 *** REVIEWS *** ACGIH TLV-Not classifiable as a human carcinogen DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 ACGIH TLV-STEL 19 mg/m3 (3 ppm) DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 ACGIH TLV-TWA 12 mg/m3 (2 ppm) DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 TOXICOLOGY REVIEW JRPMAP Journal of Reproductive Medicine. (2 Jacklynn Ct., St. Louis, MO 63132) V.3- 1969- Volume(issue)/page/year: 12,27,1974 TOXICOLOGY REVIEW NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB293-503 *** 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 MSHA STANDARD-air:TWA 2 ppm (12 mg/m3) DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: 3,37,1971 OSHA PEL (Gen Indu):8H TWA 2 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1910.1000,1994 OSHA PEL (Construc):8H TWA 2 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1926.55,1994 OSHA PEL (Shipyard):8H TWA 2 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1915.1000,1993 OSHA PEL (Fed Cont):8H TWA 2 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 41,50-204.50,1994 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-AUSTRALIA:TWA 2 ppm (12 mg/m3);STEL 3 ppm (18 mg/m3) JAN 1993 OEL-AUSTRIA:TWA 2 ppm (13 mg/m3) JAN 1993 OEL-BELGIUM:TWA 2 ppm (12 mg/m3);STEL 3 ppm (19 mg/m3) JAN 1993 OEL-DENMARK:TWA 2 ppm (12 mg/m3) JAN 1993 OEL-FINLAND:TWA 0.3 ppm (2 mg/m3);STEL 0.9 ppm (6 mg/m3) JAN 1993 OEL-FRANCE:TWA 2 ppm (12 mg/m3) JAN 1993 OEL-GERMANY:TWA 2 ppm (13 mg/m3) JAN 1993 OEL-THE NETHERLANDS:TWA 2 ppm (12 mg/m3) JAN 1993 OEL-THE PHILIPPINES:TWA 2 ppm (12 mg/m3) JAN 1993 OEL-RUSSIA:STEL 3 mg/m3 JAN 1993 OEL-SWITZERLAND:TWA 2 ppm (13 mg/m3) JAN 1993 OEL-UNITED KINGDOM:TWA 2 ppm (12 mg/m3);STEL 3 ppm (18 mg/m3) JAN 1993 OEL IN BULGARIA, COLOMBIA, JORDAN, KOREA check ACGIH TLV OEL IN NEW ZEALAND, SINGAPORE, VIETNAM check ACGIH TLV *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH RECOMMENDED EXPOSURE LEVEL (REL) : NIOSH REL TO CAMPHOR, synthetic-air:10H TWA 2 mg/m3 REFERENCE : NIOSH* National Institute for Occupational Safety and Health, U.S. Dept. of Health, Education, and Welfare, Reports and Memoranda. Volume(issue)/page/year: DHHS #92-100,1992 NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 15800 No. of Facilities: 8356 (estimated) No. of Industries: 68 No. of Occupations: 63 No. of Employees: 95578 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X1190 No. of Facilities: 25 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 427 (estimated) No. of Female Employees: 176 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 15800 No. of Facilities: 9166 (estimated) No. of Industries: 101 No. of Occupations: 87 No. of Employees: 153554 (estimated) No. of Female Employees: 53187 (estimated)

(±)-樟脑(合成)安全信息

[ 符号 ]:

GHS02, GHS07, GHS08

[ 信号词 ]:
Warning

[ 危害声明 ]:
H228-H302 + H332-H371

[ 警示性声明 ]:
P210-P260-P301 + P312 + P330-P370 + P378

[ 靶器官 ]:
Lungs

[ 个人防护装备 ]:
dust mask type N95 (US);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

[ 危害码 (欧洲) ]:
F:Flammable

[ 风险声明 (欧洲) ]:
R11;R36/37/38

[ 安全声明 (欧洲) ]:
S16-S26-S37/39

[ 危险品运输编码 ]:
UN 2717 4.1/PG 3

[ WGK德国 ]:
1

[ RTECS号 ]:
EX1225000

[ 包装等级 ]:
III

[ 危险类别 ]:
4.1

[ 海关编码 ]:
2914291000

(±)-樟脑(合成)合成路线

详细合成路线

(±)-樟脑(合成)上下游产品

(±)-樟脑(合成)上游产品

(±)-樟脑(合成)下游产品

(±)-樟脑(合成)制备

【方法一】
1.樟脑油提纯法樟脑存在于樟树中，取樟树的干、根、枝、叶经水蒸气蒸馏得樟脑油，将其减压分馏得到油樟脑和各种香精油，油樟脑经升华提纯即得精制樟脑。2.合成法以松节油为原料，提取其中的蒎烯，经异构化得到莰烯，再经酯化、水解、脱氢而得樟脑。莰烯酯化反应可在搪玻璃反应锅中进行。在硫酸催化下，莰烯与乙酸或甲酸进行酯化，反应温度38℃，加硫酸时保持45-48℃，滴加硫酸时间2-3h。反应完成后，加入40%液碱，于140℃、0.2-0.25MPa下反应6-8h得异龙脑。以二甲苯溶解后用水洗涤，然后在碱式碳酸铜作用下脱氢转变为樟脑，反应时加适量消石灰，使其在微碱性中进行。脱氢所得的粗樟脑用升华提纯，得合成樟脑。按GB 4895-85 ，一级品樟脑含量≥96%，熔点174℃。原料消耗定额：松节油1700kg/t、乙酸600kg/t。

(±)-樟脑(合成)海关

[ 海关编码 ]: 2914291000

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