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Lapachol

Lapachol structure

CAS No:
84-79-7
Formula:
C15H14O3
Chemical Name:
Lapachol
Synonyms:
1,4-Naphthalenedione,2-hydroxy-3-(3-methyl-2-buten-1-yl)-;Lapachol;1,4-Naphthoquinone,2-hydroxy-3-(3-methyl-2-butenyl)-;1,4-Naphthalenedione,2-hydroxy-3-(3-methyl-2-butenyl)-;2-Hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthalenedione;C.I. 75490;Bethabarra Wood;C.I. Natural Yellow 16;2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone;Ipe-tobacco Wood;Lapachol Wood;Surinam Greenheart Wood;Taiguic acid;Taigu Wood;Tecomin;NSC 11905;Greenhartin;2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione;NSC 629756;2-Hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae). Lapachol shows anti-infection and antitumor activity[1]

Lapachol is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae. It has a role as a plant metabolite, an antineoplastic agent, an antibacterial agent and an anti-inflammatory agent. It is a hydroxy-1,4-naphthoquinone and an olefinic compound.

Lapachol Basic Attributes

Molecular Weight：

242.27

Exact Mass：

242.27

EC Number：

201-563-7

UNII：

B221938VB6

NSC Number：

629756|11905

DSSTox ID：

DTXSID6049430

HScode：

2914690090

Characteristics

PSA：

54.4

XLogP3：

2.8

Appearance：

white to yellow powder

Density：

1.2±0.1 g/cm3

Melting Point：

139.5 °C

Boiling Point：

325.09°C (rough estimate)

Flash Point：

203.9±24.4 °C

Refractive Index：

1.606

Water Solubility：

ethanol: soluble10mg/mL, clear, light yellow to yellow

Toxicity：

LD50 in male, female BALB/c mice (g/kg): 0.487; 0.792 orally (Morrison)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

20/21/22-36/37/38

safety instructions：

26-36

RTECS Number：

QL8750000

Marks：

Precautionary statement(s)：

P261-P280-P305 + P351 + P338

Hazard Statements：

H302 + H312 + H332-H315-H319-H335

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)|Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)|Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)|Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)|Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)|Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)

MeSH Entry Terms：

2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphtho-quinone

Lapachol Use and Manufacturing

It was used in the synthesis of the lapachol metal complexes.

Computed Properties

Molecular Weight:242.27
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:242.094294304
Monoisotopic Mass:242.094294304
Topological Polar Surface Area:54.4
Heavy Atom Count:18
Complexity:439
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Shandong zhishang chemical Co.,Ltd Contact Supplier

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CI 75490;NATURAL YELLOW 16

CAS No.: 84-79-7

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CN
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LAPACHOL

CAS No.: 84-79-7

Grade: industrial Grade

Content: 98%

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