Cas no 84-79-7 (Lapachol)

Lapachol structure
Lapachol structure
Product Name:Lapachol
CAS No:84-79-7
MF:C15H14O3
MW:242.269864559174
MDL:MFCD00001679
CID:723111
PubChem ID:24848565
Update Time:2024-10-26

Lapachol Chemical and Physical Properties

Names and Identifiers

    • 1,4-Naphthalenedione,2-hydroxy-3-(3-methyl-2-buten-1-yl)-
    • Lapachol
    • LAPACHOL(RG)
    • Greenharten
    • Greenhartin
    • Taigu Wood
    • taiguicacid
    • Tecomin
    • Bethabarra wood
    • Lapachol wood
    • Taiguic acid
    • IPE-tobacco wood
    • C.I. Natural Yellow 16
    • Lapachic acid
    • Surinam greenheart wood
    • Zlut prirodni 16
    • Tecomin (VAN)
    • C.I. 75490
    • 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone
    • Zlut prirodni 16 [Czech]
    • NSC11905
    • NSC629756
    • 2-Hydroxy-3-(3-methylbut-2-enyl)-1,4-naphthoquinone
    • 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphth
    • 1,4-Naphthalenedione, 2-hydroxy-3-(3-methyl-2-butenyl)- (9CI)
    • 1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)- (7CI, 8CI)
    • 2-Hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthalenedione (ACI)
    • Lapachol (6CI)
    • 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione
    • 2-Hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione
    • NSC 11905
    • NSC 629756
    • 4-hydroxy-3-(3-methylbut-2-enyl)-1,2-naphthoquinone
    • 4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
    • ConMedNP.2435
    • ConMedNP.2436
    • 3-(3-methylbut-2-enyl)-4-oxidanyl-naphthalene-1,2-dione
    • Tox21_202948
    • NSC-11905
    • CHEBI:6377
    • DivK1c_000594
    • Oprea1_717083
    • NCIMech_000076
    • DTXCID5029390
    • UNII-B221938VB6
    • Natural Yellow-?16
    • 2-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione
    • NINDS_000594
    • CI 75490
    • AMY40588
    • HMS1921B06
    • NCGC00094931-06
    • NS00021374
    • 4-08-00-02487 (Beilstein Handbook Reference)
    • SCHEMBL157255
    • DTXSID6049430
    • AKOS032948320
    • 84-79-7
    • CAS-84-79-7
    • AC-8971
    • LAPACHOL [MI]
    • NCI60_000587
    • CI75490
    • 1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)-
    • bmse000989
    • NCGC00260494-01
    • s5684
    • 2-Hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthalenedione
    • Groenhartin
    • EINECS 201-563-7
    • HMS501N16
    • NCGC00094931-02
    • SR-05000002489
    • SPBio_001341
    • BRN 2051889
    • PD087478
    • NCI60_000457
    • NSC-11905; NSC 11905; NSC11905
    • Spectrum5_001873
    • SCHEMBL157256
    • BCP24022
    • Lapachol, 98%
    • 1,4-Naphthalenedione, 2-hydroxy-3-(3-methyl-2-butenyl)-
    • NCGC00094931-04
    • SDCCGMLS-0066666.P001
    • Q739601
    • A863979
    • IDI1_000594
    • SR-05000002489-1
    • CHEMBL15193
    • MFCD00001679
    • WLN: L66 BV EVJ CQ D2UY1&1
    • B221938VB6
    • BSPBio_002416
    • HY-N6961
    • HMS3869D03
    • NCGC00094931-01
    • NSC-629756
    • FT-0649649
    • AKOS015951424
    • SPECTRUM1501204
    • Cancer Chemother Rep (part 2) 4: 11 (1974)
    • AS-35308
    • Spectrum2_001451
    • Spectrum3_000768
    • 4-hydroxy-3-(3-methylbut-2-en-1-yl)-1,2-dihydronaphthalene-1,2-dione
    • NCGC00094931-03
    • KBio3_001636
    • 2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione
    • Lapachoic acid
    • 2-Hydroxy-3-(3-methyl-2-butenyl)naphthoquinone #
    • CS-W020951
    • CCG-35464
    • CCRIS 745
    • 1, 2-hydroxy-3-(3-methyl-2-butenyl)-
    • KBio1_000594
    • CWPGNVFCJOPXFB-UHFFFAOYSA-N
    • MDL： MFCD00001679
    • Inchi： 1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,18H,8H2,1-2H3
    • InChI Key： CIEYTVIYYGTCCI-UHFFFAOYSA-N
    • SMILES： O=C1C2C(=CC=CC=2)C(=O)C(C/C=C(\C)/C)=C1O
    • BRN： 2051889

Computed Properties

  • Exact Mass: 242.09400
  • Monoisotopic Mass: 242.094294304g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 2
  • Complexity: 439
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 54.4
  • Surface Charge: 0
  • Tautomer Count: 98
  • XLogP3: 2.8

Experimental Properties

  • Color/Form: Yellow powder
  • Density: 1.2077 (rough estimate)
  • Melting Point: 141-143?°C (lit.)
  • Boiling Point: 398.6°C at 760 mmHg
  • Refractive Index: 1.5740 (estimate)
  • Solubility: ethanol: soluble10mg/mL, clear, light yellow to yellow
  • PSA: 54.37000
  • LogP: 3.23400
  • Merck: 13,5382
  • Solubility: Not determined

Lapachol Security Information

  • Symbol: GHS07
  • Signal Word：Warning
  • Hazard Statement： H302-H312-H315-H319-H332-H335
  • Warning Statement： P261-P280-P305 + P351 + P338
  • Hazardous Material transportation number：NONH for all modes of transport
  • WGK Germany：3
  • Hazard Category Code： 20/21/22-36/37/38
  • Safety Instruction： S26; S36
  • RTECS：QL8750000
  • Hazardous Material Identification： Xn
  • Toxicity：LD50 in male, female BALB/c mice (g/kg): 0.487; 0.792 orally (Morrison)
  • Storage Condition：2-8°C
  • Risk Phrases：R20/21/22

Lapachol Customs Data

  • HS CODE：2914690090
  • Customs Data：

    China Customs Code:

    2914690090

    Overview:

    2914690090 Other Quinones. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:5.5% general tariff:30.0%

    Summary:

    2914690090 other quinones.Supervision conditions:None.VAT:17.0%.Tax rebate rate:9.0%.MFN tariff:5.5%.General tariff:30.0%

Lapachol Pricemore >>

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Lapachol Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Oxalic acid Solvents: 1,4-Dioxane ;  60 h, 100 °C
Reference
Synthesis of pharmacologically important naphthoquinones and anticancer activity of 2-benzyllawsone through DNA topoisomerase-II inhibition
Kumar, Balagani Sathish; Ravi, Kusumoori; Verma, Amit Kumar; Fatima, Kaneez; Hasanain, Mohammad; et al, Bioorganic & Medicinal Chemistry, 2017, 25(4), 1364-1373

Production Method 2

Reaction Conditions
1.1 Reagents: Formic acid ,  Oxygen Solvents: Ethanol ,  Water ;  3 h, 200 °C; 3 - 3000 psi
Reference
A new method to prepare 3-alkyl-2-hydroxy-1,4-naphthoquinones: synthesis of lapachol and phthiocol
Ferreira, Sabrina Baptista; Rodrigues da Rocha, David; Carneiro, Jose Walkimar M.; Santos, Wilson Costa; Ferreira, Vitor Francisco, Synlett, 2011, (11), 1551-1554

Production Method 3

Reaction Conditions
1.1 Reagents: Pyridine ,  Sodium iodide Solvents: Dimethyl sulfoxide ;  rt; 5 h, rt → 45 °C
1.2 Reagents: Water ;  20 min, cooled
Reference
Synthesis of β-Lapachone
Sun, Min; Wei, Hong-tao; Cai, Jin; Ji, Min, Zhongguo Xinyao Zazhi, 2008, 17(18), 1598-1599

Production Method 4

Reaction Conditions
1.1 Reagents: Potassium iodide Solvents: Dimethyl sulfoxide ;  3 h, rt → 140 °C
Reference
Iron(III) Chloride Catalyzed Formation of 3,4-Dihydro-2H-pyrans from α-Alkylated 1,3-Dicarbonyls. Selective Synthesis of α- and β-Lapachone
Watson, Rebecca B.; Golonka, Alexander N.; Schindler, Corinna S., Organic Letters, 2016, 18(6), 1310-1313

Production Method 5

Reaction Conditions
Reference
Development of a microemulsion loaded with epoxy-α-lapachone against Leishmania (Leishmania) amazonensis murine infection
Peixoto, Juliana Figueiredo; Goncalves-Oliveira, Luiz Filipe; Souza-Silva, Franklin; Cortes, Luzia Monteiro de Castro; Dias-Lopes, Geovane; et al, International Journal of Pharmaceutics (Amsterdam, 2023, 636,

Production Method 6

Reaction Conditions
1.1 Reagents: Formic acid Solvents: Ethanol ,  Water ;  3 h, 200 °C
Reference
Molecular mechanism of action of new 1,4-naphthoquinones tethered to 1,2,3-1H-triazoles with cytotoxic and selective effect against oral squamous cell carcinoma
Cavalcanti Chipoline, Ingrid; Carolina Carvalho da Fonseca, Anna; Ribeiro Machado da Costa, Gabriella; Pereira de Souza, Michele; Won-Held Rabelo, Vitor; et al, Bioorganic Chemistry, 2020, 101,

Production Method 7

Reaction Conditions
1.1 Reagents: tert-Butyl hydroperoxide Catalysts: Tetrabutylammonium iodide Solvents: Tetrahydrofuran ,  Water ;  24 h, 120 °C
1.2 Reagents: Sodium sulfite Solvents: Water
Reference
Tetrabutylammonium iodide catalyzed hydroxylation of naphthoquinone derivatives with tert-butyl hydroperoxide as an oxidant
Yu, Dong; Chen, Xu-Ling; Ai, Bai-Ru; Zhang, Xiao-Mei; Wang, Ji-Yu, Tetrahedron Letters, 2018, 59(40), 3620-3623

Production Method 8

Reaction Conditions
1.1 Reagents: Triethylamine ,  Sodium iodide Solvents: Dimethyl sulfoxide ;  1 h, rt; 6 h, 70 °C
Reference
Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase
Calil, Felipe A. ; David, Juliana S.; Chiappetta, Estela R. C.; Fumagalli, Fernando; Mello, Rodrigo B.; et al, European Journal of Medicinal Chemistry, 2019, 167, 357-366

Production Method 9

Reaction Conditions
1.1 Catalysts: 1-Adamantanecarboxylic acid ,  Tetrakis(triphenylphosphine)palladium ;  1 h, reflux
Reference
Palladium-catalyzed allylation of 2-hydroxy-1,4-naphthoquinone. Application to the preparation of lapachol
Kazantzi, Georgia; Malamidou-Xenikaki, Elizabeth; Spyroudis, Spyros, Synlett, 2007, (3), 427-430

Lapachol Raw materials

Lapachol Preparation Products

Lapachol Suppliers

Amadis Chemical Company Limited
Gold Member
Audited Supplier Audited Supplier
(CAS:84-79-7)Lapachol
Order Number:A863979
Stock Status:in Stock
Quantity:1g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 08:43
Price ($):421.0

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Amadis Chemical Company Limited
(CAS:84-79-7)Lapachol
A863979
Purity:99%
Quantity:1g
Price ($):421.0
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