MedKoo Biosciences

Totarol
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 584784

CAS#: 511-15-9

Description: Totarol is a diterpene originally isolated from P. totara that has diverse biological activities, including antibacterial, antioxidant, and neuroprotective properties.

Chemical Structure

Totarol

CAS# 511-15-9

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 584784
Name: Totarol
CAS#: 511-15-9
Chemical Formula: C20H30O
Exact Mass: 286.23
Molecular Weight: 286.460
Elemental Analysis: C, 83.86; H, 10.56; O, 5.59

Price and Availability

Size	Price	Availability
25mg	USD 210	Ready to ship
50mg	USD 350	Ready to ship
100mg	USD 555	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Totarol; (+)-Totarol

IUPAC/Chemical Name: (4bS,8aS)-4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-2-phenanthrenol

InChi Key: ZRVDANDJSTYELM-FXAWDEMLSA-N

InChi Code: 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/t17-,20+/m0/s1

SMILES Code: OC1=CC=C2[C@@]3(C)CCCC(C)(C)[C@]3([H])CCC2=C1C(C)C

Appearance: Solid powder

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot# C21B10B07

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Totarol that has diverse biological activities, including antibacterial, antioxidant, and neuroprotective properties.
In vitro activity:	In this study, whether totarol possessed an additional neuroprotective activity in vitro was determined in primary rat cerebellar granule neuronal cells (CGCs). To investigate the Nrf2/ARE activating properties of totarol, Nrf2 and HO-1 expressions were measured. Totarol time-dependently enhanced Nrf2 protein expression in CGCs under normoxic conditions (Fig. 3A). In addition, totarol increased HO-1 expression in a time-dependent and dose-dependent manner in CGCs under normoxic conditions. Reference: Toxicol Appl Pharmacol. 2015 Dec 1;289(2):142-54. https://pubmed.ncbi.nlm.nih.gov/26440581/
In vivo activity:	In a model of acute cerebral ischemic injury in Sprague-Dawley rats, produced by occlusion of the middle cerebral artery for 2h followed by 22 h or 46 h of reperfusion, totarol significantly reduced infarct volume and improved the neurological deficit. In this model, totarol increased HO-1 expression and the activities of GSH and SOD. These observations suggest that totarol may be a novel activator of the Akt/HO-1 pathway protecting against ischemic stroke through reduction of oxidative stress. Reference: Toxicol Appl Pharmacol. 2015 Dec 1;289(2):142-54. https://pubmed.ncbi.nlm.nih.gov/26440581/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	3.0	10.50
	Ethanol	2.0	7.00

Preparing Stock Solutions

The following data is based on the product molecular weight 286.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Gao Y, Xu X, Chang S, Wang Y, Xu Y, Ran S, Huang Z, Li P, Li J, Zhang L, Saavedra JM, Liao H, Pang T. Totarol prevents neuronal injury in vitro and ameliorates brain ischemic stroke: Potential roles of Akt activation and HO-1 induction. Toxicol Appl Pharmacol. 2015 Dec 1;289(2):142-54. doi: 10.1016/j.taap.2015.10.001. Epub 2015 Oct 9. PMID: 26440581. 2. Jaiswal R, Beuria TK, Mohan R, Mahajan SK, Panda D. Totarol inhibits bacterial cytokinesis by perturbing the assembly dynamics of FtsZ. Biochemistry. 2007 Apr 10;46(14):4211-20. doi: 10.1021/bi602573e. Epub 2007 Mar 10. PMID: 17348691.
In vitro protocol:	1. Gao Y, Xu X, Chang S, Wang Y, Xu Y, Ran S, Huang Z, Li P, Li J, Zhang L, Saavedra JM, Liao H, Pang T. Totarol prevents neuronal injury in vitro and ameliorates brain ischemic stroke: Potential roles of Akt activation and HO-1 induction. Toxicol Appl Pharmacol. 2015 Dec 1;289(2):142-54. doi: 10.1016/j.taap.2015.10.001. Epub 2015 Oct 9. PMID: 26440581. 2. Jaiswal R, Beuria TK, Mohan R, Mahajan SK, Panda D. Totarol inhibits bacterial cytokinesis by perturbing the assembly dynamics of FtsZ. Biochemistry. 2007 Apr 10;46(14):4211-20. doi: 10.1021/bi602573e. Epub 2007 Mar 10. PMID: 17348691.
In vivo protocol:	1. Gao Y, Xu X, Chang S, Wang Y, Xu Y, Ran S, Huang Z, Li P, Li J, Zhang L, Saavedra JM, Liao H, Pang T. Totarol prevents neuronal injury in vitro and ameliorates brain ischemic stroke: Potential roles of Akt activation and HO-1 induction. Toxicol Appl Pharmacol. 2015 Dec 1;289(2):142-54. doi: 10.1016/j.taap.2015.10.001. Epub 2015 Oct 9. PMID: 26440581.

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1. Short, W.F., and Stromberg, H. Totarol. Part I J. Chem. Soc. 0, 516-520 (1937).

2. Kubo, I., Muroi, H., and Himehima, M. Antibacterial activity of totarol and its potentiation J. Nat. Prod. 55(10), 1436-1440 (1992).

3. Haraguchi, H., Oike, S., Muroi, H., et al. Mode of antibacterial action of totarol, a diterpene from Podocarpus nagi Planta Med. 62(2), 122-125 (1996).

4. Haraguchi, H., Ishikawa, H., and Kubo, I. Antioxidative action of diterpenoids from Podocarpus nagi Planta Med. 63(3), 213-215 (1997).

5. Gao, Y., Xu, X., Chang, S., et al. Totarol prevents neuronal injury in vitro and ameliorates brain ischemic stroke: Potential roles of Akt activation and HO-1 induction Toxicol. Appl. Pharmacol. 289(2), 142-154 (2015).

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