82508-31-4,MFCD01746346
Catalog No.:AA00G2AF

82508-31-4 | pseudolaric acid B

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
≥98%
in stock  
$120.00   $84.00
- +
250mg
98%
in stock  
$280.00   $196.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA00G2AF
Chemical Name:
pseudolaric acid B
CAS Number:
82508-31-4
Molecular Formula:
C23H28O8
Molecular Weight:
432.4636
MDL Number:
MFCD01746346
SMILES:
COC(=O)C1=CC[C@@]23[C@@](CC1)(OC(=O)C)[C@@H](CC2)[C@@](OC3=O)(C)/C=C/C=C(/C(=O)O)\C
Properties
Computed Properties
 
Complexity:
913  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
2  
Formal Charge:
0  
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0  
Rotatable Bond Count:
7  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
2.3  

Downstream Synthesis Route
(1R,7S,8S,9R)-7-Acetoxy-9-((1E,3E)-4-methoxymethoxycarbonyl-penta-1,3-dienyl)-9-methyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-ene-4-carboxylicacidmethylester 
  82508-31-4 

[1]TetrahedronLetters,2002,vol.43,p.4095-4098

(1R,4S,7S,8S,9R)-7-Acetoxy-9-((1E,3E)-4-methoxymethoxycarbonyl-penta-1,3-dienyl)-9-methyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridecane-4-carboxylicacidmethylester 
  82508-31-4   
(1R,7S,8S,9R)-7-Acetoxy-9-((1E,3E)-4-methoxymethoxycarbonyl-penta-1,3-dienyl)-9-methyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-ene-4-carboxylicacidmethylester 

[1]TetrahedronLetters,2002,vol.43,p.4095-4098

71-23-8    82508-31-4   
(1R,7S,8R,9R)-9-((1E,3E)-4-Carboxy-penta-1,3-dienyl)-7-hydroxy-9-methyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-ene-4-carboxylicacidpropylester 

[1]BioorganicandMedicinalChemistry,2003,vol.11,p.4577-4584

64-17-5    82508-31-4   
(1R,7S,8R,9R)-9-((1E,3E)-4-Carboxy-penta-1,3-dienyl)-7-hydroxy-9-methyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-ene-4-carboxylicacidethylester 

[1]BioorganicandMedicinalChemistry,2003,vol.11,p.4577-4584

74-89-5    82508-31-4   
(2E,4E)-5-((1R,7S,8R,9R)-7-Hydroxy-9-methyl-4-methylcarbamoyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-en-9-yl)-2-methyl-penta-2,4-dienoicacid 
 
(2E,4E)-5-((1R,7S,8S,9R)-7-Acetoxy-9-methyl-4-methylcarbamoyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-en-9-yl)-2-methyl-penta-2,4-dienoicacid 

[1]BioorganicandMedicinalChemistry,2003,vol.11,p.4577-4584

Literature

Title: Biosynthesis of the microtubule-destabilizing diterpene pseudolaric acid B from golden larch involves an unusual diterpene synthase.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20170131

Title: Newly discovered angiogenesis inhibitors and their mechanisms of action.

Journal: Acta pharmacologica Sinica 20120901

Title: Interaction of pseudolaric acid B with the colchicine site of tubulin.

Journal: Biochemical pharmacology 20120815

Title: Pseudolaric acid B induces apoptosis via proteasome-mediated Bcl-2 degradation in hormone-refractory prostate cancer DU145 cells.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20120601

Title: Angiogenesis inhibition and cell cycle arrest induced by treatment with Pseudolarix acid B alone or combined with 5-fluorouracil.

Journal: Acta biochimica et biophysica Sinica 20120601

Title: Topical application of Pseudolaric acid B improve DNFB-induced contact hypersensitivity via regulating the balance of Th1/Th17/Treg cell subsets.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20120411

Title: In vitro synergy of pseudolaric acid B and fluconazole against clinical isolates of Candida albicans.

Journal: Mycoses 20110901

Title: Pseudolaric acid B suppresses T lymphocyte activation through inhibition of NF-kappaB signaling pathway and p38 phosphorylation.

Journal: Journal of cellular biochemistry 20090901

Title: Induction of G2/M arrest by pseudolaric acid B is mediated by activation of the ATM signaling pathway.

Journal: Acta pharmacologica Sinica 20090401

Title: Evaluation of the interaction of bioactive compounds in Cortex Pseudolarix and Radix Stephaniae by the microdialysis probe coupled with high performance liquid chromatography-mass spectrometry.

Journal: Journal of chromatography. A 20090313

Title: Total synthesis of (-)-pseudolaric acid B.

Journal: Journal of the American Chemical Society 20081203

Title: Protein tyrosine kinase, JNK, and ERK involvement in pseudolaric acid B-induced apoptosis of human breast cancer MCF-7 cells.

Journal: Acta pharmacologica Sinica 20080901

Title: Bcl-2 family proteins were involved in pseudolaric acid B-induced autophagy in murine fibrosarcoma L929 cells.

Journal: Journal of pharmacological sciences 20080701

Title: Pseudolaric acid B induces apoptosis, senescence, and mitotic arrest in human breast cancer MCF-7.

Journal: Acta pharmacologica Sinica 20071201

Title: Total synthesis of (-)-pseudolaric acid B.

Journal: Journal of the American Chemical Society 20071128

Title: Herbal diterpenoids induce growth arrest and apoptosis in colon cancer cells with increased expression of the nonsteroidal anti-inflammatory drug-activated gene.

Journal: European journal of pharmacology 20070315

Title: Involvement of JNK-initiated p53 accumulation and phosphorylation of p53 in pseudolaric acid B induced cell death.

Journal: Experimental & molecular medicine 20060831

Title: Pseudolaric acid B induces apoptosis via activation of c-Jun N-terminal kinase and caspase-3 in HeLa cells.

Journal: Experimental & molecular medicine 20041231

Title: A tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acids.

Journal: The Journal of organic chemistry 20030530

Title: Pseudolaric acid analogs as a new class of peroxisome proliferator-activated receptor agonists.

Journal: Planta medica 20020801

Title: Antifungal evaluation of pseudolaric acid B, a major constituent of Pseudolarix kaempferi.

Journal: Journal of natural products 19950101

Title: Zhou BN, et al. Some progress on the chemistry of natural bioactive terpenoids from Chinese medicinal plants. Mem Inst Oswaldo Cruz. 1991;86 Suppl 2:219-26.

Title: Wang WC, et al. [Endocrine activity of pseudolaric acids A and B and their effects on sex hormones, prostaglandins, uteri, and fetuses Zhongguo Yao Li Xue Bao. 1991 Mar;12(2):187-90.

Title: Wei N, et al. The immunosuppressive activity of pseudolaric acid B on T lymphocytes in vitro. Phytother Res. 2013 Jul;27(7):980-5.

Title: Yu J, et al. Pseudolaric acid B inhibits the secretion of hepatitis B virus. Oncol Rep. 2017 Jan;37(1):519-525.

Title: Yu J, et al. Pseudolaric acid B activates autophagy in MCF-7 human breast cancer cells to prevent cell death. Oncol Lett. 2016 Mar;11(3):1731-1737.

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Tags:82508-31-4 Molecular Formula|82508-31-4 MDL|82508-31-4 SMILES|82508-31-4 pseudolaric acid B
Catalog No.: AA00G2AF
82508-31-4,MFCD01746346
82508-31-4 | pseudolaric acid B
Pack Size: 1mg
Purity: ≥98%
in stock
$120.00 $84.00
Pack Size: 250mg
Purity: 98%
in stock
$280.00 $196.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA00G2AF
Chemical Name: pseudolaric acid B
CAS Number: 82508-31-4
Molecular Formula: C23H28O8
Molecular Weight: 432.4636
MDL Number: MFCD01746346
SMILES: COC(=O)C1=CC[C@@]23[C@@](CC1)(OC(=O)C)[C@@H](CC2)[C@@](OC3=O)(C)/C=C/C=C(/C(=O)O)\C
Properties
Complexity: 913  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 4  
Defined Bond Stereocenter Count: 2  
Formal Charge: 0  
Heavy Atom Count: 31  
Hydrogen Bond Acceptor Count: 8  
Hydrogen Bond Donor Count: 1  
Isotope Atom Count: 0  
Rotatable Bond Count: 7  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 2.3  
Downstream Synthesis Route
(1R,7S,8S,9R)-7-Acetoxy-9-((1E,3E)-4-methoxymethoxycarbonyl-penta-1,3-dienyl)-9-methyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-ene-4-carboxylicacidmethylester 
  82508-31-4 

[1]TetrahedronLetters,2002,vol.43,p.4095-4098

(1R,4S,7S,8S,9R)-7-Acetoxy-9-((1E,3E)-4-methoxymethoxycarbonyl-penta-1,3-dienyl)-9-methyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridecane-4-carboxylicacidmethylester 
  82508-31-4   
(1R,7S,8S,9R)-7-Acetoxy-9-((1E,3E)-4-methoxymethoxycarbonyl-penta-1,3-dienyl)-9-methyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-ene-4-carboxylicacidmethylester 

[1]TetrahedronLetters,2002,vol.43,p.4095-4098

71-23-8    82508-31-4   
(1R,7S,8R,9R)-9-((1E,3E)-4-Carboxy-penta-1,3-dienyl)-7-hydroxy-9-methyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-ene-4-carboxylicacidpropylester 

[1]BioorganicandMedicinalChemistry,2003,vol.11,p.4577-4584

64-17-5    82508-31-4   
(1R,7S,8R,9R)-9-((1E,3E)-4-Carboxy-penta-1,3-dienyl)-7-hydroxy-9-methyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-ene-4-carboxylicacidethylester 

[1]BioorganicandMedicinalChemistry,2003,vol.11,p.4577-4584

74-89-5    82508-31-4   
(2E,4E)-5-((1R,7S,8R,9R)-7-Hydroxy-9-methyl-4-methylcarbamoyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-en-9-yl)-2-methyl-penta-2,4-dienoicacid 
 
(2E,4E)-5-((1R,7S,8S,9R)-7-Acetoxy-9-methyl-4-methylcarbamoyl-11-oxo-10-oxa-tricyclo6.3.2.01,7tridec-3-en-9-yl)-2-methyl-penta-2,4-dienoicacid 

[1]BioorganicandMedicinalChemistry,2003,vol.11,p.4577-4584

Literature fold

Title: Biosynthesis of the microtubule-destabilizing diterpene pseudolaric acid B from golden larch involves an unusual diterpene synthase.

Journal: Proceedings of the National Academy of Sciences of the United States of America20170131

Title: Newly discovered angiogenesis inhibitors and their mechanisms of action.

Journal: Acta pharmacologica Sinica20120901

Title: Interaction of pseudolaric acid B with the colchicine site of tubulin.

Journal: Biochemical pharmacology20120815

Title: Pseudolaric acid B induces apoptosis via proteasome-mediated Bcl-2 degradation in hormone-refractory prostate cancer DU145 cells.

Journal: Toxicology in vitro : an international journal published in association with BIBRA20120601

Title: Angiogenesis inhibition and cell cycle arrest induced by treatment with Pseudolarix acid B alone or combined with 5-fluorouracil.

Journal: Acta biochimica et biophysica Sinica20120601

Title: Topical application of Pseudolaric acid B improve DNFB-induced contact hypersensitivity via regulating the balance of Th1/Th17/Treg cell subsets.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences20120411

Title: In vitro synergy of pseudolaric acid B and fluconazole against clinical isolates of Candida albicans.

Journal: Mycoses20110901

Title: Pseudolaric acid B suppresses T lymphocyte activation through inhibition of NF-kappaB signaling pathway and p38 phosphorylation.

Journal: Journal of cellular biochemistry20090901

Title: Induction of G2/M arrest by pseudolaric acid B is mediated by activation of the ATM signaling pathway.

Journal: Acta pharmacologica Sinica20090401

Title: Evaluation of the interaction of bioactive compounds in Cortex Pseudolarix and Radix Stephaniae by the microdialysis probe coupled with high performance liquid chromatography-mass spectrometry.

Journal: Journal of chromatography. A20090313

Title: Total synthesis of (-)-pseudolaric acid B.

Journal: Journal of the American Chemical Society20081203

Title: Protein tyrosine kinase, JNK, and ERK involvement in pseudolaric acid B-induced apoptosis of human breast cancer MCF-7 cells.

Journal: Acta pharmacologica Sinica20080901

Title: Bcl-2 family proteins were involved in pseudolaric acid B-induced autophagy in murine fibrosarcoma L929 cells.

Journal: Journal of pharmacological sciences20080701

Title: Pseudolaric acid B induces apoptosis, senescence, and mitotic arrest in human breast cancer MCF-7.

Journal: Acta pharmacologica Sinica20071201

Title: Total synthesis of (-)-pseudolaric acid B.

Journal: Journal of the American Chemical Society20071128

Title: Herbal diterpenoids induce growth arrest and apoptosis in colon cancer cells with increased expression of the nonsteroidal anti-inflammatory drug-activated gene.

Journal: European journal of pharmacology20070315

Title: Involvement of JNK-initiated p53 accumulation and phosphorylation of p53 in pseudolaric acid B induced cell death.

Journal: Experimental & molecular medicine20060831

Title: Pseudolaric acid B induces apoptosis via activation of c-Jun N-terminal kinase and caspase-3 in HeLa cells.

Journal: Experimental & molecular medicine20041231

Title: A tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acids.

Journal: The Journal of organic chemistry20030530

Title: Pseudolaric acid analogs as a new class of peroxisome proliferator-activated receptor agonists.

Journal: Planta medica20020801

Title: Antifungal evaluation of pseudolaric acid B, a major constituent of Pseudolarix kaempferi.

Journal: Journal of natural products19950101

Title: Zhou BN, et al. Some progress on the chemistry of natural bioactive terpenoids from Chinese medicinal plants. Mem Inst Oswaldo Cruz. 1991;86 Suppl 2:219-26.

Title: Wang WC, et al. [Endocrine activity of pseudolaric acids A and B and their effects on sex hormones, prostaglandins, uteri, and fetuses Zhongguo Yao Li Xue Bao. 1991 Mar;12(2):187-90.

Title: Wei N, et al. The immunosuppressive activity of pseudolaric acid B on T lymphocytes in vitro. Phytother Res. 2013 Jul;27(7):980-5.

Title: Yu J, et al. Pseudolaric acid B inhibits the secretion of hepatitis B virus. Oncol Rep. 2017 Jan;37(1):519-525.

Title: Yu J, et al. Pseudolaric acid B activates autophagy in MCF-7 human breast cancer cells to prevent cell death. Oncol Lett. 2016 Mar;11(3):1731-1737.

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