CAS 84-79-7|Lapachol
| Common Name | Lapachol | ||
|---|---|---|---|
| CAS Number | 84-79-7 | Molecular Weight | 242.270 |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 390.1±42.0 °C at 760 mmHg |
| Molecular Formula | C15H14O3 | Melting Point | 141-143ºC(lit.) |
| MSDS | ChineseUSA | Flash Point | 203.9±24.4 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | Lapachol |
|---|---|
| Synonym | More Synonyms |
Lapachol BiologicalActivity
| Description | Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae). Lapachol shows anti-infection and antitumor activity[1] |
|---|---|
| Related Catalog | Research Areas >>CancerResearch Areas >>InfectionSignaling Pathways >>Anti-infection >>FungalSignaling Pathways >>Anti-infection >>Bacterial |
| References | [1]. Hidayat Hussain, Karsten Krohn,etc.Lapachol: an overview.ARKIVOC 2007 (ii) 145-171 |
Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 390.1±42.0 °C at 760 mmHg |
| Melting Point | 141-143ºC(lit.) |
| Molecular Formula | C15H14O3 |
| Molecular Weight | 242.270 |
| Flash Point | 203.9±24.4 °C |
| Exact Mass | 242.094299 |
| PSA | 54.37000 |
| LogP | 4.08 |
| Vapour Pressure | 0.0±0.9 mmHg at 25°C |
| Index of Refraction | 1.606 |
| InChIKey | CWPGNVFCJOPXFB-UHFFFAOYSA-N |
| SMILES | CC(C)=CCC1=C(O)c2ccccc2C(=O)C1=O |
| Water Solubility | ethanol: soluble10mg/mL, clear, light yellow to yellow |
Toxicological Information
CHEMICAL IDENTIFICATION |
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
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302 + H312 + H332-H315-H319-H335 |
| Precautionary Statements | P261-P280-P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Faceshields;Gloves |
| Hazard Codes | Xn: Harmful; |
| Risk Phrases | R20/21/22 |
| Safety Phrases | 26-36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | QL8750000 |
| HS Code | 2914690090 |
Customs
| HS Code | 2914690090 |
|---|---|
| Summary | 2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0% |
Articles28
More Articles| Quinones derived from plant secondary metabolites as anti-cancer agents. Anticancer Agents Med. Chem. 13(3) , 456-63, (2013) Quinones are plant-derived secondary metabolites that present some anti-proliferation and anti-metastasis effects in various cancer types both in vitro and in vivo. This review focuses on the anti-can... | |
| Organometallic anticancer complexes of lapachol: metal centre-dependent formation of reactive oxygen species and correlation with cytotoxicity. Chem. Commun. (Camb.) 49(32) , 3348-50, (2013) Organometallic Ru(II), Os(II) and Rh(III) complexes of lapachol induce apoptosis in human tumour cell lines in the low μM range by a mode of action involving oxidative stress, especially in the case o... | |
| Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol Bioorg. Med. Chem. 18 , 2621-30, (2010) A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been in... |
Synonyms
| 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 |
