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Totarol

Catalog Number
ACM511159-3
CAS
511-15-9
Structure
IUPAC Name
4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol
Synonyms
2-Phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-, (4bS-trans)-
Molecular Weight
286.46
Molecular Formula
C20H30O
Canonical SMILES
CC(C)C1=C(C=CC2=C1CCC3C2(CCCC3(C)C)C)O
InChI
InChI=1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3
InChI Key
ZRVDANDJSTYELM-UHFFFAOYSA-N
Melting Point
128-132°C(lit.)
Purity
98%
Appearance
Powder
Active Content
95%
Physical State
Solid
Typical Applications
Use as antioxidant.
Use as antibacterial agent.
Spec Sheet
Case Study

Totarol Prevents In Vitro Neuronal Injury and Improves Ischemic Stroke

Totarol Prevents <em>In Vitro</em> Neuronal Injury and Improves Ischemic Stroke Gao, Y., Xu, X., Chang, S., et al. (2015). Toxicology and applied pharmacology, 289(2), 142-154.

The natural product totarol is a phenolic diterpene compound with potent antimicrobial activity. In this study, we investigated whether totarol has additional neuroprotective activities in vitro and in vivo.
Totarol Prevents In Vitro Neuronal Injury and Improves Ischemic Stroke
We found that totarol can prevent neuronal death induced by glutamate, oxygen, and glucose deprivation in primary rat cerebellar granule neurons and cerebral cortical neurons. Totarol increased the phosphorylation of Akt and GSK-3β, and the protein expression of Nrf2 and heme oxygenase-1 (HO-1), and suppressed oxidative stress by increasing GSH and SOD activities. The PI3K/Akt inhibitor LY294002 blocked the neuroprotective effects of totarol by inhibiting totarol-induced HO-1 expression and changes in GSH and SOD activities. The HO-1 inhibitor ZnPPIX also prevented the totarol-mediated increase in GSH and SOD activities. In a Sprague-Dawley rat model of acute cerebral ischemic injury, totarol significantly reduced infarct volume and improved neurological deficits following 2 hours of middle cerebral artery occlusion and 22 or 46 hours of reperfusion. In this model, totarol increased the expression of HO-1 as well as the activities of GSH and SOD. These observations suggest that totarol may be a novel activator of the Akt/HO-1 pathway, and protects against ischemic stroke by reducing oxidative stress.

The Application of Totarol as a Natural Antimicrobial Coating on Implants to Prevent Peri-implantitis

The Application of Totarol as a Natural Antimicrobial Coating on Implants to Prevent Peri-implantitis Xu, Z., Krajewski, S., Weindl, T., Loeffler, R., et al. (2020). Materials Science and Engineering: C, 110, 110701.

Peri-implantitis is the most significant threat to the long-term survival of dental implants. Totarol coatings have shown remarkable antimicrobial effects against oral bacteria and can inhibit oral biofilm formation for up to one month. This makes totarol a promising candidate as a coating for dental abutments or implants to prevent peri-implantitis during the healing phase after implant placement.
The Antimicrobial Effects of Totarol Coated Titanium Against Mixed Oral Bacteria
Incubation with a mixed culture of oral bacteria in an agitated system showed that the totarol-coated Ti exhibited significant bactericidal effects for up to 48 hours. For the totarol-coated Ti discs, the initial adhesion of oral bacteria after 1 hour and 4 hours of incubation showed similar densities compared to the controls. However, the totarol coating significantly inhibited the proliferation of the mixed oral bacterial isolates. Before 48 hours of culture, a dense green biofilm had formed on the control Ti discs. In contrast, only sparse bacterial chains were found on the totarol coating. According to the crystal violet staining and SEM results, the biomass of the 24-hour and 48-hour oral bacterial biofilms grown on the totarol coating displayed significantly lower densities on the silicon wafers and Ti surfaces compared to the uncoated controls (p<0.05). This indicates that the totarol-coated Ti exhibited both contact-killing and biofilm growth-inhibiting effects against various oral biofilms within 48 hours of incubation.

Custom Q&A

What is the molecular formula of Totarol?

The molecular formula of Totarol is C20H30O.

What is the molecular weight of Totarol?

The molecular weight of Totarol is 286.5 g/mol.

Where is Totarol found in nature?

Totarol is a natural product found in Podocarpus affinis, Podocarpus rumphii, and other organisms.

What is the IUPAC name of Totarol?

The IUPAC name of Totarol is (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol.

What are the synonyms for Totarol?

Some synonyms for Totarol include 511-15-9, (+)-Totarol, and CHEBI:69241.

What is the InChIKey of Totarol?

The InChIKey of Totarol is ZRVDANDJSTYELM-FXAWDEMLSA-N.

What is the CAS number of Totarol?

The CAS number of Totarol is 511-15-9.

How many hydrogen bond donor counts are there in Totarol?

There is one hydrogen bond donor in Totarol.

What is the topological polar surface area of Totarol?

The topological polar surface area of Totarol is 20.2 Ų.

What is the complexity value of Totarol?

The complexity value of Totarol is 385.

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