84-79-7

• 常用中文名：黄钟花醌
• 常用英文名：Lapachol
• CAS号：84-79-7
• 分子式：C₁₅H₁₄O₃
• 分子量：242.270
• 相关类别： 有机原料 醌类化合物
• 发布时间：2018-03-01 08:00:00
• 更新时间：2024-01-03 18:03:55
• Lapachol是一种萘醌,最早从Tabebuia avellanedae(紫葳科)中分离得到,具有一定的抗感染和抗肿瘤活性。

名称

• 中文名: 拉帕醇
• 英文名: Lapachol
• 中文别名: 黄钟花醌
• 英文别名: 1,4-Naphthalenedione, 2-hydroxy-3-(3-methyl-2-buten-1-yl)-; EINECS 201-563-7; MFCD00001679; 2-Hydroxy-3-(3-méthyl-2-butèn-1-yl)-1,4-naphtoquinone; taiguicacid; Greenhartin; 2-Hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthoquinone; Greenharten; 2-Hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthochinone; Lapachol; Taigu Wood; 1,4-Naphthoquinone, 2-hydroxy-3- (3-methyl-2-butenyl)-; 1,4-Naphthalenedione, 2-hydroxy-3- (3-methyl-2-butenyl)-; 2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione; Tecomin; 2-Hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-naphthoquinone

物化性质

• 密度: 1.2±0.1 g/cm3
• 沸点: 390.1±42.0 °C at 760 mmHg
• 熔点: 141-143ºC(lit.)
• 分子式: C₁₅H₁₄O₃
• 分子量: 242.270
• 闪点: 203.9±24.4 °C
• 精确质量: 242.094299
• PSA: 54.37000
• LogP: 4.08
• 外观性状: 白色至黄色粉末
• 蒸汽压: 0.0±0.9 mmHg at 25°C
• 折射率: 1.606
• 储存条件:

  常温

  阴凉干燥处保存

• 稳定性:

  常温常压下稳定

• 水溶解性: ethanol: soluble10mg/mL, clear, light yellow to yellow
• 分子结构:

  1、 摩尔折射率：67.61

  2、 摩尔体积（m³/mol）：196.0

  3、 等张比容（90.2K）：524.3

  4、 表面张力（dyne/cm）：51.1

  5、 介电常数：无可用

  6、 偶极距（10 ^-24cm ³）：无可用

  7、 极化率：26.80

• 计算化学:

  1.疏水参数计算参考值（XlogP）:2.8

  2.氢键供体数量:1

  3.氢键受体数量:3

  4.可旋转化学键数量:2

  5.互变异构体数量:98

  6.拓扑分子极性表面积54.4

  7.重原子数量:18

  8.表面电荷:0

  9.复杂度:439

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1. 性状：有色物质

  2. 密度（g/mL,25℃）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：141-143

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,5.2kPa）：未确定

  7. 折射率：-未确定

  8. 闪点（ºF）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（mmHg,20ºC）：未确定

  12. 饱和蒸气压（kPa,20 ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（MPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：未确定

生物活性

• 描述: Lapachol是一种萘醌,最早从Tabebuia avellanedae(紫葳科)中分离得到,具有一定的抗感染和抗肿瘤活性。
• 相关类别:
  研究领域 >> 癌症
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 真菌
  信号通路 >> 抗感染 >> 细菌
• 参考文献:

  [1]. Hidayat Hussain, Karsten Krohn,etc.Lapachol: an overview.ARKIVOC 2007 (ii) 145-171

MSDS

SECTION 1: Identification of the substance/mixture and of the company/undertaking Product identifiers Product name: Lapachol REACH No.: A registration number is not available for this substance as the substance or its uses are exempted from registration, the annual tonnage does not require a registration or the registration is envisaged for a later registration deadline. CAS-No.: 84-79-7 Relevant identified uses of the substance or mixture and uses advised against Identified uses: Laboratory chemicals, Manufacture of substances SECTION 2: Hazards identification Classification of the substance or mixture Classification according to Regulation (EC) No 1272/2008 Acute toxicity, Inhalation (Category 4), H332 Acute toxicity, Dermal (Category 4), H312 Acute toxicity, Oral (Category 4), H302 Skin irritation (Category 2), H315 Eye irritation (Category 2), H319 Specific target organ toxicity - single exposure (Category 3), H335 For the full text of the H-Statements mentioned in this Section, see Section 16. Classification according to EU Directives 67/548/EEC or 1999/45/EC Xn HarmfulR20/21/22, R36/37/38 For the full text of the R-phrases mentioned in this Section, see Section 16. Label elements Labelling according Regulation (EC) No 1272/2008 Pictogram Signal wordWarning Hazard statement(s) H302Harmful if swallowed. H312Harmful in contact with skin. H315Causes skin irritation. H319Causes serious eye irritation. H332Harmful if inhaled. H335May cause respiratory irritation. Precautionary statement(s) P261Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray. P280Wear protective gloves/ protective clothing. P305 + P351 + P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Supplemental Hazardnone Statements Other hazards - none SECTION 3: Composition/information on ingredients Substances Synonyms: Natural Yellow 16 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone Formula: C15H14O3 Molecular Weight: 242,27 g/mol CAS-No.: 84-79-7 EC-No.: 201-563-7 Hazardous ingredients according to Regulation (EC) No 1272/2008 ComponentClassificationConcentration 2-Hydroxy-3-(3-methylbut-2-enyl)-1,4-naphthoquinone CAS-No.84-79-7Acute Tox. 4; Skin Irrit. 2; Eye<= 100 % EC-No.201-563-7Irrit. 2; STOT SE 3; H302, H312, H315, H319, H332, H335 Hazardous ingredients according to Directive 1999/45/EC ComponentClassificationConcentration 2-Hydroxy-3-(3-methylbut-2-enyl)-1,4-naphthoquinone CAS-No.84-79-7Xn, R20/21/22 - R36/37/38<= 100 % EC-No.201-563-7 For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16 SECTION 4: First aid measures Description of first aid measures General advice Consult a physician. Show this safety data sheet to the doctor in attendance. If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Most important symptoms and effects, both acute and delayed The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in section 11 Indication of any immediate medical attention and special treatment needed no data available SECTION 5: Firefighting measures Extinguishing media Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special hazards arising from the substance or mixture Carbon oxides Advice for firefighters Wear self contained breathing apparatus for fire fighting if necessary. Further information no data available SECTION 6: Accidental release measures Personal precautions, protective equipment and emergency procedures Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Environmental precautions Do not let product enter drains. Methods and materials for containment and cleaning up Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal. Reference to other sections For disposal see section 13. SECTION 7: Handling and storage Precautions for safe handling Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire protection. For precautions see section 2.2. Conditions for safe storage, including any incompatibilities Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Specific end use(s) Apart from the uses mentioned in section 1.2 no other specific uses are stipulated SECTION 8: Exposure controls/personal protection Control parameters Components with workplace control parameters Exposure controls Appropriate engineering controls Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Personal protective equipment Eye/face protection Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Body Protection Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Respiratory protection For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Control of environmental exposure Do not let product enter drains. SECTION 9: Physical and chemical properties Information on basic physical and chemical properties a) AppearanceForm: solid b) Odourno data available c) Odour Thresholdno data available d) pHno data available e) Melting point/freezingMelting point/range: 141 - 143 °C - lit. point f) Initial boiling point and no data available boiling range g) Flash pointno data available h) Evapouration rateno data available i) Flammability (solid, gas) no data available j) Upper/lowerno data available flammability or explosive limits k) Vapour pressureno data available l) Vapour densityno data available m) Relative densityno data available n) Water solubilityno data available o) Partition coefficient: n- no data available octanol/water p) Auto-ignitionno data available temperature q) Decompositionno data available temperature r) Viscosityno data available s) Explosive propertiesno data available t) Oxidizing propertiesno data available Other safety information no data available SECTION 10: Stability and reactivity Reactivity no data available Chemical stability Stable under recommended storage conditions. Possibility of hazardous reactions no data available Conditions to avoid no data available Incompatible materials Strong oxidizing agents Hazardous decomposition products Other decomposition products - no data available In the event of fire: see section 5 SECTION 11: Toxicological information Information on toxicological effects Acute toxicity LD50 Oral - mouse - 487 mg/kg Remarks: Behavioral:Somnolence (general depressed activity). Diarrhoea Prolonged skin contact may cause skin irritation and/or dermatitis. Skin corrosion/irritation no data available Serious eye damage/eye irritation no data available Respiratory or skin sensitisation no data available Germ cell mutagenicity no data available Carcinogenicity IARC:No component of this product present at levels greater than or equal to 0.1% is identified as probable, possible or confirmed human carcinogen by IARC. Reproductive toxicity no data available Specific target organ toxicity - single exposure Inhalation - May cause respiratory irritation. Specific target organ toxicity - repeated exposure no data available Aspiration hazard no data available Additional Information RTECS: QL8750000 To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly investigated. SECTION 12: Ecological information Toxicity no data available Persistence and degradability no data available Bioaccumulative potential no data available Mobility in soil no data available Results of PBT and vPvB assessment PBT/vPvB assessment not available as chemical safety assessment not required/not conducted Other adverse effects no data available SECTION 13: Disposal considerations Waste treatment methods Product Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging Dispose of as unused product. SECTION 14: Transport information UN number ADR/RID: -IMDG: -IATA: - UN proper shipping name ADR/RID: Not dangerous goods IMDG: Not dangerous goods IATA:Not dangerous goods Transport hazard class(es) ADR/RID: -IMDG: -IATA: - Packaging group ADR/RID: -IMDG: -IATA: - Environmental hazards ADR/RID: noIMDG Marine pollutant: noIATA: no Special precautions for user no data available SECTION 15: Regulatory information This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006. Safety, health and environmental regulations/legislation specific for the substance or mixture no data available Chemical Safety Assessment For this product a chemical safety assessment was not carried out SECTION 16: Other information Full text of H-Statements referred to under sections 2 and 3. Acute Tox.Acute toxicity Eye Irrit.Eye irritation H302Harmful if swallowed. H312Harmful in contact with skin. H315Causes skin irritation. H319Causes serious eye irritation. H332Harmful if inhaled. H335May cause respiratory irritation. Skin Irrit.Skin irritation Full text of R-phrases referred to under sections 2 and 3 XnHarmful R20/21/22Harmful by inhalation, in contact with skin and if swallowed. R36/37/38Irritating to eyes, respiratory system and skin. Further information Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use only. The above information is believed to be correct but does not purport to be all inclusive and shall be used only as a guide. The information in this document is based on the present state of our knowledge and is applicable to the product with regard to appropriate safety precautions. It does not represent any guarantee of the properties of the product. Corporation and its Affiliates shall not be held liable for any damage resulting from handling or from contact with the above product. See and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

毒性和生态

毒理学数据: 1、 急性毒性：大鼠经口LDLo：1200mg/kg 小鼠经口LD50：487mg/kg 小鼠腹腔LD50：400mg/kg 2、 其他多剂量毒性：狗经口TDLo：24mg/kg/4W-I 猴子经口TDLo：12mg/kg/4W-I 生态学数据: 常对水是不危害的，若无政府许可，勿将材料排入周围环境 CHEMICAL IDENTIFICATION RTECS NUMBER : QL8750000 CHEMICAL NAME : 1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)- CAS REGISTRY NUMBER : 84-79-7 BEILSTEIN REFERENCE NO. : 2051889 LAST UPDATED : 199612 DATA ITEMS CITED : 5 MOLECULAR FORMULA : C15-H14-O3 MOLECULAR WEIGHT : 242.29 WISWESSER LINE NOTATION : L66 BV EVJ CQ D2UY1&1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 1200 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: 17,1,1970 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 487 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Skin and Appendages - dermatitis, other (after systemic exposure) REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 17,1,1970 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 400 mg/kg TOXIC EFFECTS : Tumorigenic - active as anti-cancer agent REFERENCE : JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 26,570,1983 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 24 gm/kg/4W-I TOXIC EFFECTS : Blood - normocytic anemia Blood - changes in other cell count (unspecified) REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 17,1,1970 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Primate - monkey DOSE/DURATION : 12 gm/kg/4W-I TOXIC EFFECTS : Related to Chronic Data - death REFERENCE : FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 26,539,1967

安全

• 符号: GHS07
• 信号词: Warning
• 危害声明: H302 + H312 + H332-H315-H319-H335
• 警示性声明: P261-P280-P305 + P351 + P338
• 个人防护装备: dust mask type N95 (US);Eyeshields;Faceshields;Gloves
• 危害码 (欧洲): Xn: Harmful;
• 风险声明 (欧洲): R20/21/22
• 安全声明 (欧洲): 26-36
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 3
• RTECS号: QL8750000
• 海关编码: 2914690090

合成路线

上下游产品

上游产品  8
83-72-7 870-63-3 107-86-8 36417-25-1
78-79-5 5690-26-6 556-82-1 15298-01-8
下游产品  10
111479-51-7 4707-32-8 4707-33-9 15297-92-4
74693-31-5 18635-24-0 85-44-9 137493-02-8
32358-83-1 195156-48-0

制备

由二元酚、酚和芳胺类氧化制取醌

海关

海关编码	2914690090
中文概述	2914690090 其他醌. 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%
Summary	2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%