Lapachol
Suppliers
Names
[ CAS No. ]:
84-79-7
[ Name ]:
Lapachol
[Synonym ]:
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
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
[ Water Solubility ]:
ethanol: soluble10mg/mL, clear, light yellow to yellow
MSDS
Toxicological Information
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
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
Synthetic Route
Precursor & DownStream
Precursor
DownStream
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%
Articles
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...
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...
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...