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(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol (CAS 511-15-9)

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Alternate Names:
Totarol
Application:
(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol is a naturally- occurring diterpene that exhibits potent antimicrobial activity
CAS Number:
511-15-9
Purity:
≥95%
Molecular Weight:
286.45
Molecular Formula:
C20H30O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol is a synthetic organic compound that is of interest in the field of organic and synthetic chemistry research. This compound′s complex structure, characterized by a trans-fused ring system and multiple chiral centers, makes it a useful subject for studies in stereoselective synthesis and chiral resolution techniques. Researchers focus on its synthetic pathways to develop new methods for constructing phenanthrene derivatives, which are important in the synthesis of natural products and novel materials. The presence of the isopropyl group and the alcohol functionality in (4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol allows for further derivatization, making it a versatile intermediate for the preparation of more complex organic molecules. Additionally, its structure is studied for its physical properties, such as optical activity, which is relevant in the development of optically active materials and in the field of molecular electronics.


(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol (CAS 511-15-9) References

  1. Potentiation of methicillin activity against methicillin-resistant Staphylococcus aureus by diterpenes.  |  Nicolson, K., et al. 1999. FEMS Microbiol Lett. 179: 233-9. PMID: 10518721
  2. Antibacterial activity of totarol and its potentiation.  |  Kubo, I., et al. 1992. J Nat Prod. 55: 1436-40. PMID: 1453180
  3. Totarol inhibits bacterial cytokinesis by perturbing the assembly dynamics of FtsZ.  |  Jaiswal, R., et al. 2007. Biochemistry. 46: 4211-20. PMID: 17348691
  4. The antifungal compound totarol of Thujopsis dolabrata var. hondai seeds selects for fungi on seedling root surfaces.  |  Yamaji, K., et al. 2007. J Chem Ecol. 33: 2254-65. PMID: 18026796
  5. Antiparasitic, nematicidal and antifouling constituents from Juniperus berries.  |  Samoylenko, V., et al. 2008. Phytother Res. 22: 1570-6. PMID: 19067375
  6. Synthesis, biological evaluation and mechanistic studies of totarol amino alcohol derivatives as potential antimalarial agents.  |  Tacon, C., et al. 2012. Bioorg Med Chem. 20: 893-902. PMID: 22196513
  7. Inhibitory effect of totarol on exotoxin proteins hemolysin and enterotoxins secreted by Staphylococcus aureus.  |  Shi, C., et al. 2015. World J Microbiol Biotechnol. 31: 1565-73. PMID: 26193949
  8. The synergy of berberine chloride and totarol against Staphylococcus aureus grown in planktonic and biofilm cultures.  |  Guo, N., et al. 2015. J Med Microbiol. 64: 891-900. PMID: 26272283
  9. Totarol prevents neuronal injury in vitro and ameliorates brain ischemic stroke: Potential roles of Akt activation and HO-1 induction.  |  Gao, Y., et al. 2015. Toxicol Appl Pharmacol. 289: 142-54. PMID: 26440581
  10. Effects of Ultrasound Treatment on Physiochemical Properties and Antimicrobial Activities of Whey Protein-Totarol Nanoparticles.  |  Ma, S., et al. 2017. J Food Prot. 80: 1657-1665. PMID: 28876131
  11. Antibacterial activity and mode of action of totarol against Staphylococcus aureus in carrot juice.  |  Shi, C., et al. 2018. J Food Sci Technol. 55: 924-934. PMID: 29487434
  12. Application of totarol as natural antibacterial coating on dental implants for prevention of peri-implantitis.  |  Xu, Z., et al. 2020. Mater Sci Eng C Mater Biol Appl. 110: 110701. PMID: 32204015
  13. Totarol, a natural diterpenoid, induces selective antitumor activity in SGC-7901 human gastric carcinoma cells by triggering apoptosis, cell cycle disruption and suppression of cancer cell migration.  |  Xu, T., et al. 2021. J BUON. 26: 640. PMID: 34077024
  14. Mode of antibacterial action of totarol, a diterpene from Podocarpus nagi.  |  Haraguchi, H., et al. 1996. Planta Med. 62: 122-5. PMID: 8657742
  15. Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus.  |  Muroi, H. and Kubo, I. 1996. J Appl Bacteriol. 80: 387-94. PMID: 8849640

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol, 100 mg

sc-226866
100 mg
$179.00

(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol, 500 mg

sc-226866A
500 mg
$714.00

(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol, 1 g

sc-226866B
1 g
$1295.00

(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol, 2 g

sc-226866C
2 g
$2040.00