1. chem960
  2. 82508-31-4

Introduction

Pseudolaric acid B is a diterpenoid acid isolated from the root of Pseudolarix kaempferi (Pinaceae). It has anticancer \ antifungal \ antifertility activities and immunosuppressive activity on T lymphocytes Conclusion: Pseudolaric acid B inhibits the secretion of hepatitis B virus (HBV) through apoptosis and cell cycle arrest Pseudolaric acid B induces autophagy

Names and Identifiers

  • Pseudolaric acid B
  • (-)-Pseudolaric Acid B
  • 1H-4,9a-Ethanocyclohepta[c]pyran-7-carboxylicacid,4a-(acetyloxy)-3-[(1E,3E)-4-carboxy-1,3-pentadien-1-yl]-3,4,4a,5,6,9-hexahydro-3-methyl-1-oxo-,7-methyl ester, (3R,4S,4aS,9aR)-
  • PSEUDOLARIC ACID
  • PSEUDOLARIC ACID B(AS)
  • 2-Phenylpyridine
  • PLAB
  • PseudolaricAcid?B
  • Pseudolarix acid B
  • O-Acetylpseudolaric acid C
  • (2Z,4E)-5-[(8R)-7-Acetyloxy-4-methoxycarbonyl-9-methyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-3-en-
  • Pseudolaric-Acid-B
  • Pseudolaric acid b(pba)
  • BCP07962
  • Y0174
  • 508P314
  • (2E,4E)-5-[(1S,7S,8S,9R)-7-acetyloxy-4-methoxycarbonyl-9-methyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tri
  • Pseudolaric Acid B
  • 1H-4,9a-Ethanocyclohepta[c]pyran-7-carboxylic acid, 4a-(acetyloxy)-3-(4-carboxy-1,3-pentadienyl)-3,4,4a,5,6,9-hexahydro-3-methyl-1-oxo-, 7-methyl ester, [3R-[3α(1E,3E),4α,4aα,9aα]]- (ZCI)
  • 1H-4,9a-Ethanocyclohepta[c]pyran-7-carboxylic acid, 4a-(acetyloxy)-3-[(1E,3E)-4-carboxy-1,3-pentadienyl]-3,4,4a,5,6,9-hexahydro-3-methyl-1-oxo-, 7-methyl ester, (3R,4S,4aS,9aR)- (9CI)
  • (-)-Pseudolaric acid B
  • NSC 615488
  • SR-01000946401
  • EX-A680
  • CHEMBL218534
  • AKOS030573539
  • (2E,4E)-5-(acetoxy-methoxycarbonyl-methyl-oxo-[?]yl)-2-methyl-penta-2,4-dienoic acid
  • SCHEMBL16426061
  • HMS3648B11
  • CS-0009706
  • (2E,4E)-5-[(7S,1R,8R)-7-Acetyloxy-4-(methoxycarbonyl)-9-methyl-10-oxa-11-oxotricyclo[6.3.2.0<1,7>]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
  • CCG-269040
  • HY-N6939
  • (2E,4E)-5-((3R,4S,4aS,9aR)-4a-acetoxy-7-(methoxycarbonyl)-3-methyl-1-oxo-3,4,4a,5,6,9-hexahydro-1H-4,9a-ethanocyclohepta[c]pyran-3-yl)-2-methylpenta-2,4-dienoic acid
  • 82508-31-4
  • s5373
  • SR-01000946401-1
  • PSEUDOLARICACIDB
  • AKOS032948344
  • RL05141
  • CID 71307573
  • AKOS015897130
  • 1H-4,9a-Ethanocyclohepta(c)pyran-7-carboxylic acid, 4a-(acetyloxy)-3-(4-carboxy-1,3-pentadienyl)3,4,4a,5,6,9-hexahydro-3-methyl-1-oxo-, 7-methyl ester, (3-alpha(1E,3E),4-alpha,4a-alpha,9a-alpha)-(-)-
  • AC-6065
  • DTXSID801033696
  • HSDB 8110
  • (2E,4E)-5-[(1R,7S,8S,9R)-7-acetyloxy-4-methoxycarbonyl-9-methyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
  • (2E,4E)-5-[(1R,7S,8S,9R)-7-acetyloxy-4-methoxycarbonyl-9-methyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
  • (2E,4E)-5-[(1R,7S,8S,9R)-7-acetyloxy-4-methoxycarbonyl-9-methyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
  • MDL:MFCD26960905
  • InChIKey:VDGOFNMYZYBUDT-YDRCMHEVSA-N
  • Inchi:1S/C23H28O8/c1-14(18(25)26)6-5-10-21(3)17-9-12-22(20(28)31-21)11-7-16(19(27)29-4)8-13-23(17,22)30-15(2)24/h5-7,10,17H,8-9,11-13H2,1-4H3,(H,25,26)/b10-5+,14-6+/t17-,21+,22+,23-/m0/s1
  • SMILES:O([C@]12CCC(C(=O)OC)=CC[C@@]31CC[C@H]2[C@@](C)(/C=C/C=C(\C)/C(=O)O)OC3=O)C(=O)C

Chemical and Physical Properties

Computed Properties

  • Exact Mass: 432.5g/mol
  • Surface Charge: 0
  • XLogP3: 2.3
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 8
  • Rotatable Bond Count: 7
  • Monoisotopic Mass: 432.178418g/mol
  • Monoisotopic Mass: 432.178418g/mol
  • Topological Polar Surface Area: 116Ų
  • Heavy Atom Count: 31
  • Complexity: 913
  • Isotope Atom Count: 0
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 2
  • Undefined Bond Stereocenter Count: 0
  • Covalently-Bonded Unit Count: 1
  • Surface Charge: 0

Experimental Properties

  • Dissociation Constants:pKa = 4.14 (est)
  • LogP: 2.87060
  • PSA: 116.20000
  • Refractive Index: 1.4480 (estimate)
  • Boiling Point: 466.14°C (rough estimate)
  • Melting Point: 166°C
  • Flash Point: 208.8±25.0 °C
  • Solubility: Not available
  • Density: 1.2108 (rough estimate)
Security Information
  • Symbol: GHS06 GHS06 GHS08 GHS08
  • WGK Germany:3
  • Safety Instruction:36/37-45
  • Dangerous goods sign: T T
  • Hazardous Material transportation number:UN 2811 6.1 / PGIII
  • Hazard Statement:H301-H361
  • Warning Statement:P281-P301+P310
  • Storage Condition:2-8°C
  • Hazard Category Code:25-62
  • Signal Word:Danger

Synthetic Circuit

Synthetic Circuit 1
Reaction Conditions
1.1 Catalysts: Scandium triflate Solvents: Acetic anhydride ;  2 h, 0 °C
2.1 Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ;  15 min, rt
3.1 Reagents: Diisopropylethylamine Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: N-Methyl-2-pyrrolidone ;  17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557
Synthetic Circuit 2
Reaction Conditions
1.1 Reagents: Zinc acetate Solvents: Methanol ,  Chloroform ;  16 h, 60 °C
2.1 Reagents: Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine Catalysts: Sodium ascorbate ,  Copper sulfate Solvents: Methanol ,  Chloroform ,  Dimethyl sulfoxide ,  Water ;  4 h, 30 °C
3.1 Solvents: Dimethyl sulfoxide ,  Water ;  300 s, pH 7.4, rt
Reference
Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids
Watanabe, Kenji ; et al, Journal of Organic Chemistry, 2021, 86(17), 11822-11834
Synthetic Circuit 3
Reaction Conditions
1.1 Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ;  15 min, rt
2.1 Reagents: Diisopropylethylamine Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: N-Methyl-2-pyrrolidone ;  17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557
Synthetic Circuit 4
Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Diethyl ether ;  15 min, rt; 3 h, reflux; reflux → 23 °C
1.2 23 °C; 20 h, reflux; reflux → 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  0 °C
2.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  rt; 20 h, reflux; reflux → 23 °C
3.1 Reagents: Diisopropylethylamine Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: N-Methyl-2-pyrrolidone ;  rt; 22 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2008, 130(48), 16424-16434
Synthetic Circuit 5
Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  30 min, 0 °C
1.2 Solvents: Tetrahydrofuran ;  5 h, 0 °C → rt
1.3 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Acetic acid Solvents: Water ;  0.5 h, 60 °C; 60 °C → rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ;  pH 7
2.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  1 h, rt
2.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  7 h, rt
3.1 Reagents: 4-(Dimethylamino)pyridine ;  8 h, rt
4.1 -
Reference
Total synthesis of pseudolaric acid A
Geng, Zhe; et al, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 6
Reaction Conditions
1.1 Reagents: 1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Catalysts: 4-(Dimethylamino)pyridine Solvents: Dimethylformamide ;  20 h, 30 °C
2.1 Reagents: Zinc acetate Solvents: Methanol ,  Chloroform ;  16 h, 60 °C
3.1 Reagents: Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine Catalysts: Sodium ascorbate ,  Copper sulfate Solvents: Methanol ,  Chloroform ,  Dimethyl sulfoxide ,  Water ;  4 h, 30 °C
4.1 Solvents: Dimethyl sulfoxide ,  Water ;  300 s, pH 7.4, rt
Reference
Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids
Watanabe, Kenji ; et al, Journal of Organic Chemistry, 2021, 86(17), 11822-11834
Synthetic Circuit 7
Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  20 h, reflux; reflux → 23 °C
1.2 Reagents: Potassium carbonate ,  Hydrochloric acid Solvents: Dichloromethane ,  Water ;  pH 1, 23 °C
2.1 Reagents: Diisopropylethylamine Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: N-Methyl-2-pyrrolidone ;  17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557
Synthetic Circuit 8
Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Methanol
Reference
Thermodynamic theory of gases on solid interface adsorption isotherms
Li, Xueliang; et al, Huaxue Tongbao, 1995, (7), 57-61
Synthetic Circuit 9
Reaction Conditions
Reference
Total synthesis of pseudolaric acid A
Geng, Zhe; et al, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 10
Reaction Conditions
1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0 °C; 20 min, 23 °C
2.1 Catalysts: Scandium triflate Solvents: Acetic anhydride ;  2 h, 0 °C
3.1 Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ;  15 min, rt
4.1 Reagents: Diisopropylethylamine Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: N-Methyl-2-pyrrolidone ;  17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557
Synthetic Circuit 11
Reaction Conditions
1.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  30 min, rt
2.1 -
Reference
Formal Synthesis of Pseudolaric Acid B
Mori, Naoki, Synlett, 2020, 31(9), 907-910
Synthetic Circuit 12
Reaction Conditions
1.1 Reagents: 4-(Dimethylamino)pyridine ;  8 h, rt
2.1 -
Reference
Total synthesis of pseudolaric acid A
Geng, Zhe; et al, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 13
Reaction Conditions
1.1 Reagents: Acetic acid Solvents: Water ;  0.5 h, 60 °C; 60 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  pH 7
1.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  1 h, rt
1.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  7 h, rt
2.1 Reagents: 4-(Dimethylamino)pyridine ;  8 h, rt
3.1 -
Reference
Total synthesis of pseudolaric acid A
Geng, Zhe; et al, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 14
Reaction Conditions
1.1 Reagents: Diisopropylethylamine Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: N-Methyl-2-pyrrolidone ;  17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557
Synthetic Circuit 15
Reaction Conditions
1.1 Reagents: Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine Catalysts: Sodium ascorbate ,  Copper sulfate Solvents: Methanol ,  Chloroform ,  Dimethyl sulfoxide ,  Water ;  4 h, 30 °C
2.1 Solvents: Dimethyl sulfoxide ,  Water ;  300 s, pH 7.4, rt
Reference
Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids
Watanabe, Kenji ; et al, Journal of Organic Chemistry, 2021, 86(17), 11822-11834
Synthetic Circuit 16
Reaction Conditions
1.1 Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ;  rt; 15 min, rt
2.1 Reagents: Diisopropylethylamine Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: N-Methyl-2-pyrrolidone ;  rt; 22 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2008, 130(48), 16424-16434
Synthetic Circuit 17
Reaction Conditions
1.1 Solvents: Dimethyl sulfoxide ,  Water ;  300 s, pH 7.4, rt
Reference
Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids
Watanabe, Kenji ; et al, Journal of Organic Chemistry, 2021, 86(17), 11822-11834
Synthetic Circuit 18
Reaction Conditions
1.1 Catalysts: Scandium triflate Solvents: Acetic anhydride ;  0 °C; 2 h, 0 °C
2.1 Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ;  rt; 15 min, rt
3.1 Reagents: Diisopropylethylamine Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: N-Methyl-2-pyrrolidone ;  rt; 22 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2008, 130(48), 16424-16434
Synthetic Circuit 19
Reaction Conditions
1.1 Reagents: Cerium trichloride Solvents: Diethyl ether ,  Tetrahydrofuran ;  30 min, -78 °C
1.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C
1.3 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  30 min, rt
3.1 -
Reference
Formal Synthesis of Pseudolaric Acid B
Mori, Naoki, Synlett, 2020, 31(9), 907-910
Synthetic Circuit 20
Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Diethyl ether ;  3 h, reflux; reflux → 23 °C
1.2 20 h, reflux; reflux → 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  0 °C
2.1 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  20 h, reflux; reflux → 23 °C
2.2 Reagents: Potassium carbonate ,  Hydrochloric acid Solvents: Dichloromethane ,  Water ;  pH 1, 23 °C
3.1 Reagents: Diisopropylethylamine Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: N-Methyl-2-pyrrolidone ;  17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557

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S5373-5mg99.90%现货5mg¥1204.315 Sep. 2023
S5373-25mg99.90%现货25mg¥3661.6326 Apr. 2022
Brand:bomeibioSupplier:合肥博美生物科技有限责任公司
No.PurityStockSpecificationPriceupdate timeoperate
BZP0802-20mgHPLC≥98%现货20mg¥380元15 Sep. 2023
Brand:安捷凯Supplier:武汉安捷凯生物医药科技有限公司
No.PurityStockSpecificationPriceupdate timeoperate
ajcn4964-20mg98%现货20mg¥2341.0007 Sep. 2023
Brand:aladdinSupplier:上海阿拉丁生化科技股份有限公司
No.PurityStockSpecificationPriceupdate timeoperate
P107673-20mg分析标准品,98%现货20mg¥512.9001 Sep. 2023
Brand:scbtSupplier:圣克鲁斯生物技术
No.PurityStockSpecificationPriceupdate timeoperate
sc-203221A-1 mg≥95%1mg¥557.0011 Jul. 2023
sc-203221-100 µg≥95%100µg¥218.0011 Jul. 2023
sc-203221-100µg≥95%100µg¥218.0005 Sep. 2023
sc-203221A-1mg≥95%1mg¥557.0005 Sep. 2023
Brand:trcSupplier:TRC
No.PurityStockSpecificationPriceupdate timeoperate
P839505-10mg0.010mg$178.0017 May. 2023
P839505-25mg0.025mg$207.0017 May. 2023
P839505-100mg0.0100mg$414.0017 May. 2023
Brand:九鼎Supplier:上海贤鼎生物科技有限公司
No.PurityStockSpecificationPriceupdate timeoperate
L-LF496-5mg分析标准品,98%现货5mg¥275.006 Mar. 2023
L-LF496-5mg分析标准品,98%现货5mg¥275.028 Sep. 2022
L-JA330-20mg98%现货20mg¥1126.028 Feb. 2022
Brand:麦克林Supplier:上海麦克林生化科技有限公司
No.PurityStockSpecificationPriceupdate timeoperate
P815934-100mg98%上海仓库:现货/北方仓库:-/南方仓库:-100mg¥2,698.0028 Sep. 2022
Brand:chemsceneSupplier:ChemScence
No.PurityStockSpecificationPriceupdate timeoperate
CS-0009706-100mg99.47%In-stock100mg$1067.026 Apr. 2022
CS-0009706-50mg99.47%In-stock50mg$627.026 Apr. 2022
CS-0009706-10mg99.47%In-stock10mg$209.026 Apr. 2022
CS-0009706-5mg99.47%In-stock5mg$121.026 Apr. 2022
Brand:topscienceSupplier:上海陶术生物科技有限公司
No.PurityStockSpecificationPriceupdate timeoperate
T1922-100 mg99.68%上海现货100MG¥7534.0026 Apr. 2022
T1922-50 mg99.68%上海现货50mg¥5382.0026 Apr. 2022
T1922-10 mg99.68%上海现货10mg¥1772.0026 Apr. 2022
T1922-5 mg99.68%上海现货5mg¥1012.0026 Apr. 2022
T1922-2 mg99.68%上海现货2mg¥562.0026 Apr. 2022
Brand:dcchemicalSupplier:DC Chemicals
No.PurityStockSpecificationPriceupdate timeoperate
DCT-009-20 mg>98%, Standard References GradeIn stock20mg$280.028 Feb. 2022
DCT-009-20mg>98%, Standard References GradeIn stock20mg$280.015 Sep. 2023
Brand:AcmecSupplier:上海吉至生化科技有限公司
No.PurityStockSpecificationPriceupdate timeoperate
P22210-20mg现货20mg¥498.008 Sep. 2021
Brand:百灵威Supplier:百灵威科技有限公司
No.PurityStockSpecificationPriceupdate timeoperate
122452-5MG98%河北: 35MG¥ 13126 Apr. 2022
L79110880-20mg98.10%20mg¥30424 Nov. 2023
S18DCT-009-20mg≥98%20mg¥224024 Nov. 2023
A01953833-22mg22mg¥25124 Nov. 2023
A01122452-5mg98%河北:35mg¥13124 Nov. 2023
Brand:aaronSupplier:Aaron
No.PurityStockSpecificationPriceupdate timeoperate
AR00G327-100mg98%In China Stock100mg$155.0013 Dec. 2023
AR00G327-50mg98%In China Stock50mg$111.0013 Dec. 2023
AR00G327-20mg98%In China Stock20mg$84.0013 Dec. 2023
Brand:phytolabSupplier:PhytoLab
No.PurityStockSpecificationPriceupdate timeoperate
80523-1000mg≥ 98.0 %1000mg€1597525 Oct. 2023
80523-500mg≥ 98.0 %500mg€852025 Oct. 2023
80523-250mg≥ 98.0 %250mg€4526.2525 Oct. 2023
80523-50mg≥ 98.0 %50mg€958.525 Oct. 2023
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