beta-lapachone
2H-naphthol[1,2-b]pyan-5,6-dione, 3,4-dihydro-2,2-dimethyl-
 
Notes:
inhibitor of reverse transcriptase & dna polymerase; inhibitor of dna topoisomerase.
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2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione (Click)
CAS Number: 4707-32-8Picture of molecule
FDA UNII: 6N4FA2QQ6A
Beilstein Number: 0181499
MDL: MFCD01712233
XlogP3-AA: 2.20 (est)
Molecular Weight: 242.27418000
Formula: C15 H14 O3
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antimicrobial agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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IBM Patents: Obtain
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PubMed: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 381.40 °C. @ 760.00 mm Hg (est)
Flash Point: 337.00 °F. TCC ( 169.70 °C. ) (est)
logP (o/w): 2.820 (est)
Soluble in:
 water, 48.47 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antimicrobial agents
skin conditioning
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Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
beta-Lapachone ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
beta-Lapachone ≥98% (TLC)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antimicrobial agents
Recommendation for beta-lapachone usage levels up to:
 not for fragrance use.
 
Recommendation for beta-lapachone flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
ClinicalTrials.gov: search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 3885
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
Chemidplus: 0004707328
RTECS: QL6127400 for cas# 4707-32-8
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References:
 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 3885
Pubchem (sid): 135023007
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEMBL: View
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 tabebuia avellanedae
Search Trop  Picture
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Synonyms:
3,4-dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione
2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
 lapachone
2H-naphthol[1,2-b]pyan-5,6-dione, 3,4-dihydro-2,2-dimethyl-
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Articles:
PubMed: Beta-lapachone, a modulator of NAD metabolism, prevents health declines in aged mice.
PubMed: Beta-lapachone (LAPA) decreases cell viability and telomerase activity in leukemia cells: suppression of telomerase activity by LAPA.
PubMed: Beta-lapachone, a quinone isolated from Tabebuia avellanedae, induces apoptosis in HepG2 hepatoma cell line through induction of Bax and activation of caspase.
PubMed: Toxic potential of dietary genistein isoflavone and beta-lapachone on capacitation and acrosome reaction of epididymal spermatozoa.
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