Cas no 82-08-6 (Rottlerin)

Rottlerin structure
Rottlerin structure
Product Name:Rottlerin
CAS No:82-08-6
MF:C30H28O8
MW:516.538529396057
MDL:MFCD00017361
CID:724284
PubChem ID:24278679
Update Time:2024-10-27

Rottlerin Chemical and Physical Properties

Names and Identifiers

    • 2-Propen-1-one,1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-,(2E)-
    • 2-Propen-1-one,1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phe
    • pGlu-Ala-OH
    • Rottlerin
    • ROTTLERIN(RG)
    • (E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one
    • Kamalin
    • Mallotoxin
    • 1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one
    • NSC 56346
    • NSC 94525
    • (2E)-1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one (ACI)
    • 2-Propen-1-one, 1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-, (E)- (ZCI)
    • Acetophenone, 3′-[(8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl]-2′,4′,6′-trihydroxy-5′-methyl- (7CI, 8CI)
    • Rottlerin (6CI)
    • PKC-δ/PKC-θ inhibitor
    • MLS003370622
    • SMR000058242
    • 3'-((8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl)-2',4',6'-trihydroxy-5'-methyl-acetophenone
    • NSC 94525Mallotoxin
    • NCGC00025228-08
    • SR-01000076106-6
    • (E)-1-(6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-phenylprop-2-en-1-one
    • CCG-36482
    • BDBM50126829
    • (E)-1-(6-((3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl)-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl)-3-phenyl-2-propen-1-one
    • NCGC00025228-12
    • BMK1-F10
    • UNII-E29LP3ZMUH
    • NCGC00025228-19
    • NSC56346
    • Z2583131081
    • MS-29589
    • BSPBio_001080
    • NCGC00025228-10
    • IDI1_002135
    • 82-08-6
    • SCHEMBL148175
    • SR-01000076106-3
    • CHEBI:92065
    • SDCCGSBI-0051022.P002
    • Q7370686
    • HMS1990F21
    • CS-0014823
    • HY-18980
    • SCHEMBL1537089
    • MFCD00017361
    • (2E)-1-[6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-phenylprop-2-en-1-one
    • (2E)-1-(6-(3-ACETYL-2,4,6-TRIHYDROXY-5-METHYLBENZYL)-5,7-DIHYDROXY-2,2-DIMETHYL-2H-CHROMEN-8-YL)-3-PHENYLPROP-2-EN-1-ONE
    • LP01052
    • HMS3403F21
    • Tox21_501052
    • HB0561
    • Lopac0_001052
    • E29LP3ZMUH
    • NCGC00261737-01
    • NSC-94525
    • ROTTLERIN [MI]
    • NSC-56346
    • AKOS024282482
    • NCGC00025228-02
    • BRN 0070757
    • R5648 (Rottlerin)
    • LMPK12120428
    • SR-01000076106
    • BRD-K03816923-001-03-9
    • BRD-K39256324-001-01-5
    • DTXSID30231502
    • GTPL2611
    • 1-[6-(3-Acetyl-2,4,6-trihydroxy-5-methyl-benzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-phenyl-propenone
    • Mallotoxin; NSC 56346; NSC 94525
    • Acetophenone, 3'-((8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl)-2',4',6'-trihydroxy-5'-methyl-
    • BiomolKI_000058
    • 1-(6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-phenylprop-2-en-1-one
    • NSC94525
    • S7862
    • 3'-[(8-Cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl]-2',4',6'-trihydroxy-5'-methylacetophenone
    • NCGC00025228-11
    • NCGC00025228-06
    • NCGC00025228-09
    • BCBcMAP01_000019
    • NCGC00025228-04
    • (E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methyl-phenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-chromen-8-yl]-3-phenyl-prop-2-en-1-one
    • Rottlerin - CAS 82-08-6
    • NCGC00025228-05
    • HMS3263C06
    • (E)-1-[6-[(3-Acetyl-2,4,6-trihydroxy-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one
    • 5,7-dihydroxy-2,2-dimethyl-6-(2,4,6-trihydroxy-3-methyl-5-acetylbenzyl)-8-cinnamoyl-1,2-chromene
    • 5-18-05-00695 (Beilstein Handbook Reference)
    • CHEMBL34241
    • EU-0101052
    • SR-01000076106-2
    • HMS1792F21
    • 1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one
    • NCGC00025228-07
    • F88130
    • 1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one
    • HMS1362F21
    • NCGC00025228-03
    • CHEBI:8899
    • EINECS 201-395-4
    • R 5648
    • NS00015852
    • BiomolKI2_000064
    • DEZFNHCVIZBHBI-ZHACJKMWSA-N
    • GLXC-10271
    • 3'-((8-Cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl)-2',4',6'-trihydroxy-5'-methyl-acetophenone; Mallotoxin
    • DTXCID90153993
    • (E)-1-(6-((3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl)-5,7-dihydroxy-2,2-dimethylchromen-8-yl)-3-phenylprop-2-en-1-one
    • MDL： MFCD00017361
    • Inchi： 1S/C30H28O8/c1-15-24(33)19(27(36)22(16(2)31)25(15)34)14-20-26(35)18-12-13-30(3,4)38-29(18)23(28(20)37)21(32)11-10-17-8-6-5-7-9-17/h5-13,33-37H,14H2,1-4H3/b11-10+
    • InChI Key： DEZFNHCVIZBHBI-ZHACJKMWSA-N
    • SMILES： C(C1C(O)=C(CC2C(O)=C(C)C(O)=C(C(=O)C)C=2O)C(O)=C2C=CC(OC=12)(C)C)(=O)/C=C/C1C=CC=CC=1

Computed Properties

  • Exact Mass: 516.17800
  • Monoisotopic Mass: 516.17841785g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 38
  • Rotatable Bond Count: 6
  • Complexity: 921
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 630
  • XLogP3: 5.9
  • Topological Polar Surface Area: 145?2

Experimental Properties

  • Color/Form: Light reddish brown or brownish yellow flake or needle like crystals with golden luster
  • Density: 1.2051 (rough estimate)
  • Melting Point: 200 °C
  • Boiling Point: 521.39°C (rough estimate)
  • Refractive Index: 1.4900 (estimate)
  • PSA: 144.52000
  • LogP: 5.39670
  • Solubility: Soluble in ether \ chloroform \ benzene \ ethyl acetate, slightly soluble in cold ethanol \ acetic acid, almost insoluble in water

Rottlerin Security Information

  • Hazardous Material transportation number：NONH for all modes of transport
  • WGK Germany：3
  • Hazard Category Code： 20/21/22-22
  • Safety Instruction： S36/37
  • RTECS：AM6913800
  • Hazardous Material Identification： Xn
  • Storage Condition：Please store the product under the recommended conditions in the Certificate of Analysis.
  • Risk Phrases：R20/21/22

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Rottlerin Production Method

Production Method 1

Reaction Conditions
1.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin: The Sequel
Hong, Kenneth K. C.; et al, Journal of Natural Products, 2019, 82(5), 1190-1199

Production Method 2

Reaction Conditions
1.1 Reagents: Lanthanum triflate Solvents: Ethanol ,  Water ;  10 h, rt
Reference
The Practical Total Synthesis of Rottlerin and Rottlerone
Chen, Xu-Ling; et al, ChemistrySelect, 2020, 5(29), 9206-9209

Production Method 3

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Methanol ,  Water ;  rt; rt → 50 °C
1.2 Reagents: Mercury alloy, nonbase, Hg,Zn ;  5 min, 50 °C
2.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin
Hong, Kenneth K. C.; et al, Journal of Organic Chemistry, 2015, 80(21), 10668-10674

Production Method 4

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  0 °C; 28 h, rt
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  4 h, rt
3.1 Solvents: Chloroform ;  1 h, reflux
Reference
The Practical Total Synthesis of Rottlerin and Rottlerone
Chen, Xu-Ling; et al, ChemistrySelect, 2020, 5(29), 9206-9209

Production Method 5

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Methanol ;  10 h, rt
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  4 h, reflux
3.1 Solvents: Chloroform ;  0.5 h, reflux
4.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin
Hong, Kenneth K. C.; et al, Journal of Organic Chemistry, 2015, 80(21), 10668-10674

Production Method 6

Reaction Conditions
1.1 Reagents: Phosphorus oxychloride Solvents: Ethyl acetate ;  0 °C; 1 h, rt
2.1 Reagents: Hydrochloric acid ,  Sodium cyanoborohydride Solvents: Tetrahydrofuran ,  Water ;  4 h, pH 4, rt; 15 h, rt; 2 h, rt
3.1 Reagents: Lanthanum triflate Solvents: Ethanol ,  Water ;  10 h, rt
Reference
The Practical Total Synthesis of Rottlerin and Rottlerone
Chen, Xu-Ling; et al, ChemistrySelect, 2020, 5(29), 9206-9209

Production Method 7

Reaction Conditions
1.1 Reagents: Ethylenediaminediacetic acid Solvents: Chloroform ;  10 min, rt
2.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  5 min, 0 °C
2.2 2 h, rt
2.3 Reagents: Water ;  30 min, rt
3.1 Solvents: Chloroform ;  0.5 h, reflux
4.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin: The Sequel
Hong, Kenneth K. C.; et al, Journal of Natural Products, 2019, 82(5), 1190-1199

Production Method 8

Reaction Conditions
1.1 Reagents: Imidazole Solvents: Dimethylformamide ;  15 min, rt
1.2 Reagents: Pyridinium p-toluenesulfonate Solvents: Methanol ;  2 h, reflux
2.1 Reagents: Ethylenediaminediacetic acid Solvents: Chloroform ;  10 min, rt
3.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  5 min, 0 °C
3.2 2 h, rt
3.3 Reagents: Water ;  30 min, rt
4.1 Solvents: Chloroform ;  0.5 h, reflux
5.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin: The Sequel
Hong, Kenneth K. C.; et al, Journal of Natural Products, 2019, 82(5), 1190-1199

Production Method 9

Reaction Conditions
1.1 Reagents: Pyridinium p-toluenesulfonate Solvents: Methanol ;  2 h, reflux
2.1 Reagents: Ethylenediaminediacetic acid Solvents: Chloroform ;  10 min, rt
3.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  5 min, 0 °C
3.2 2 h, rt
3.3 Reagents: Water ;  30 min, rt
4.1 Solvents: Chloroform ;  0.5 h, reflux
5.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin: The Sequel
Hong, Kenneth K. C.; et al, Journal of Natural Products, 2019, 82(5), 1190-1199

Production Method 10

Reaction Conditions
1.1 Reagents: Iodine Solvents: Methanol ;  10 h, rt
2.1 Reagents: Acetic acid ,  Ethylenediamine Solvents: Chloroform ;  12 h, reflux
3.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  0 °C; 28 h, rt
4.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  4 h, rt
5.1 Reagents: Lanthanum triflate Solvents: Ethanol ,  Water ;  10 h, rt
Reference
The Practical Total Synthesis of Rottlerin and Rottlerone
Chen, Xu-Ling; et al, ChemistrySelect, 2020, 5(29), 9206-9209

Production Method 11

Reaction Conditions
1.1 Catalysts: Sulfuric acid Solvents: Ethanol ,  Water ;  18 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt; neutralized
Reference
Efficient synthesis of rottlerin and its two subunits
Li, Yangfeng; et al, Tetrahedron Letters, 2016, 57(17), 1856-1859

Production Method 12

Reaction Conditions
1.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin
Hong, Kenneth K. C.; et al, Journal of Organic Chemistry, 2015, 80(21), 10668-10674

Production Method 13

Reaction Conditions
1.1 Solvents: Chloroform ;  1 h, reflux
Reference
The Practical Total Synthesis of Rottlerin and Rottlerone
Chen, Xu-Ling; et al, ChemistrySelect, 2020, 5(29), 9206-9209

Production Method 14

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  4 h, rt
2.1 Solvents: Chloroform ;  1 h, reflux
Reference
The Practical Total Synthesis of Rottlerin and Rottlerone
Chen, Xu-Ling; et al, ChemistrySelect, 2020, 5(29), 9206-9209

Production Method 15

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  4 h, reflux
2.1 Solvents: Chloroform ;  0.5 h, reflux
3.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin
Hong, Kenneth K. C.; et al, Journal of Organic Chemistry, 2015, 80(21), 10668-10674

Production Method 16

Reaction Conditions
1.1 Solvents: Chloroform ;  0.5 h, reflux
2.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin: The Sequel
Hong, Kenneth K. C.; et al, Journal of Natural Products, 2019, 82(5), 1190-1199

Production Method 17

Reaction Conditions
1.1 Solvents: Chloroform ;  0.5 h, reflux
2.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin
Hong, Kenneth K. C.; et al, Journal of Organic Chemistry, 2015, 80(21), 10668-10674

Production Method 18

Reaction Conditions
1.1 Reagents: Hydrochloric acid ,  Sodium cyanoborohydride Solvents: Tetrahydrofuran ,  Water ;  4 h, pH 4, rt; 15 h, rt; 2 h, rt
2.1 Reagents: Lanthanum triflate Solvents: Ethanol ,  Water ;  10 h, rt
Reference
The Practical Total Synthesis of Rottlerin and Rottlerone
Chen, Xu-Ling; et al, ChemistrySelect, 2020, 5(29), 9206-9209

Production Method 19

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  5 min, 0 °C
1.2 2 h, rt
1.3 Reagents: Water ;  30 min, rt
2.1 Solvents: Chloroform ;  0.5 h, reflux
3.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin: The Sequel
Hong, Kenneth K. C.; et al, Journal of Natural Products, 2019, 82(5), 1190-1199

Production Method 20

Reaction Conditions
1.1 Reagents: Phosphorus oxychloride Solvents: Ethyl acetate ;  1 h, rt
1.2 Reagents: Water
2.1 Reagents: Hydrochloric acid Solvents: Methanol ,  Water ;  rt; rt → 50 °C
2.2 Reagents: Mercury alloy, nonbase, Hg,Zn ;  5 min, 50 °C
3.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin
Hong, Kenneth K. C.; et al, Journal of Organic Chemistry, 2015, 80(21), 10668-10674

Production Method 21

Reaction Conditions
1.1 Reagents: Acetic acid ,  Ethylenediamine Solvents: Chloroform ;  12 h, reflux
2.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  0 °C; 28 h, rt
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  4 h, rt
4.1 Solvents: Chloroform ;  1 h, reflux
Reference
The Practical Total Synthesis of Rottlerin and Rottlerone
Chen, Xu-Ling; et al, ChemistrySelect, 2020, 5(29), 9206-9209

Production Method 22

Reaction Conditions
1.1 -
2.1 Reagents: Potassium hydroxide Solvents: Methanol ;  10 h, rt
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  4 h, reflux
4.1 Solvents: Chloroform ;  0.5 h, reflux
5.1 Solvents: Toluene ;  0.5 h, reflux
Reference
The Mosaic of Rottlerin
Hong, Kenneth K. C.; et al, Journal of Organic Chemistry, 2015, 80(21), 10668-10674

Production Method 23

Reaction Conditions
1.1 Catalysts: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Dimethylformamide ;  rt; 2 h, rt
1.2 Solvents: Dimethylformamide ;  rt; 14.5 h, rt
2.1 Reagents: Iodine Solvents: Methanol ;  10 h, rt
3.1 Reagents: Acetic acid ,  Ethylenediamine Solvents: Chloroform ;  12 h, reflux
4.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  0 °C; 28 h, rt
5.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  4 h, rt
6.1 Reagents: Lanthanum triflate Solvents: Ethanol ,  Water ;  10 h, rt
Reference
The Practical Total Synthesis of Rottlerin and Rottlerone
Chen, Xu-Ling; et al, ChemistrySelect, 2020, 5(29), 9206-9209

Production Method 24

Reaction Conditions
1.1 Reagents: Boron trifluoride etherate Solvents: Acetic acid ;  3 h, reflux
2.1 Catalysts: Sulfuric acid Solvents: Ethanol ,  Water ;  18 h, rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt; neutralized
Reference
Efficient synthesis of rottlerin and its two subunits
Li, Yangfeng; et al, Tetrahedron Letters, 2016, 57(17), 1856-1859

Production Method 25

Reaction Conditions
1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0 °C; 6 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt
2.1 Catalysts: Sulfuric acid Solvents: Ethanol ,  Water ;  18 h, rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt; neutralized
Reference
Efficient synthesis of rottlerin and its two subunits
Li, Yangfeng; et al, Tetrahedron Letters, 2016, 57(17), 1856-1859

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Rottlerin Preparation Products

Rottlerin Suppliers

Amadis Chemical Company Limited
Gold Member
Audited Supplier Audited Supplier
(CAS:82-08-6)Rottlerin
Order Number:A1205243
Stock Status:in Stock
Quantity:25mg/50mg/100mg
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 03:41
Price ($):295.0/502.0/853.0

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Amadis Chemical Company Limited
(CAS:82-08-6)Rottlerin
A1205243
Purity:99%/99%/99%
Quantity:25mg/50mg/100mg
Price ($):295.0/502.0/853.0
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