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

  • 2-Hydroxy-1,4-naphoquinone
  • 3,3-Dimethylallyl bromide
  • 3-Methyl-2-butenal
  • 4-hydroxynaphthalene-1,2-dione,silver
  • isoprene
  • 1,2,3,4-Naphthalenetetrol
  • 3-Methyl-2-buten-1-ol
  • 1,4-Naphthalenedione,2-hydroxy-3-(3-hydroxy-3-methylbutyl)-

DownStream

  • 3-(3-chloro-3-methylbutyl)-4-hydroxynaphthalene-1,2-dione
  • Beta-Lapachone
  • alpha-Lapachone
  • Dehydro-alpha-lapachone
  • 2-(prop-1-en-2-yl)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
  • 2-Isopropenyl-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
  • Phthalic anhydride
  • stenocarpoquinone B
  • naphtho(1,2-b)furan-4,5-dione
  • 2-((3,3-dimethyloxiran-2-yl)methyl)-3-hydroxynaphthalene-1,4-dione

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

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...


More Articles


Related Compounds

  • lapachol
  • Hydrolapachol
  • Lapachol-acetat
  • nickel lapachol
  • Lapachol,sodium salt
  • 2-((2-(2,6-dimethylmorpholino)-2-oxoethyl)thio)-3-(2-methoxyethyl)-3H-pyrimido[5,4-b]indol-4(5H)-one
  • ethyl 4-(2-((3-(2-methoxyethyl)-4-oxo-4,5-dihydro-3H-pyrimido[5,4-b]indol-2-yl)thio)acetyl)piperazine-1-carboxylate
  • 2-((3-(2-methoxyethyl)-4-oxo-4,5-dihydro-3H-pyrimido[5,4-b]indol-2-yl)thio)-N-((tetrahydrofuran-2-yl)methyl)acetamide
  • ethyl 4-(2-((3-allyl-4-oxo-4,5-dihydro-3H-pyrimido[5,4-b]indol-2-yl)thio)acetyl)piperazine-1-carboxylate
  • 2-((3-allyl-4-oxo-4,5-dihydro-3H-pyrimido[5,4-b]indol-2-yl)thio)-N-((tetrahydrofuran-2-yl)methyl)acetamide
  • 2-((3-allyl-4-oxo-4,5-dihydro-3H-pyrimido[5,4-b]indol-2-yl)thio)-N-(3,4-dimethoxyphenethyl)acetamide
  • 2-((3-allyl-4-oxo-4,5-dihydro-3H-pyrimido[5,4-b]indol-2-yl)thio)-N-(6-methylbenzo[d]thiazol-2-yl)acetamide
  • 3-(adamantane-1-amido)-N-(4-ethylphenyl)-1-benzofuran-2-carboxamide
  • 3-benzamido-N-(4-ethylphenyl)benzofuran-2-carboxamide
  • N-(4-ethylphenyl)-3-(naphthalene-1-amido)-1-benzofuran-2-carboxamide
The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.