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MedKoo Cat#: 584784 | Name: Totarol
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Description:

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

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

Chemical Structure

Totarol
Totarol
CAS#511-15-9

Theoretical Analysis

MedKoo Cat#: 584784

Name: Totarol

CAS#: 511-15-9

Chemical Formula: C20H30O

Exact Mass: 286.2297

Molecular Weight: 286.46

Elemental Analysis: C, 83.86; H, 10.56; O, 5.59

Price and Availability

Size Price Availability Quantity
25mg USD 150.00 Ready to ship
50mg USD 250.00 Ready to ship
100mg USD 400.00 Ready to ship
200mg USD 650.00 Ready to ship
500mg USD 950.00 Ready to ship
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Related CAS #
No Data
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/
Solvent mg/mL mM
Solubility
DMSO 3.0 10.50
Ethanol 2.0 7.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

Recalculate based on batch purity %
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.
1: Jojić AA, Liga S, Uţu D, Ruse G, Suciu L, Motoc A, Şoica CM, Tchiakpe-Antal DS. Beyond Essential Oils: Diterpenes, Lignans, and Biflavonoids from Juniperus communis L. as a Source of Multi-Target Lead Compounds. Plants (Basel). 2024 Nov 17;13(22):3233. doi: 10.3390/plants13223233. PMID: 39599442; PMCID: PMC11598787. 2: Hoisang S, Jitpean S, Seesupa S, Kamlangchai P, Makpunpol T, Ngowwatana P, Chaimongkol S, Khunbutsri D, Khlongkhlaeo J, Kampa N. Evaluation of Totarol for Promoting Open Wound Healing in Dogs. Vet Sci. 2024 Sep 16;11(9):437. doi: 10.3390/vetsci11090437. PMID: 39330816; PMCID: PMC11435550. 3: Wang YT, Liu LT, Hou B, Yao CM, Wang XF, Lu B. Recent advances in studies on FtsZ inhibitors. Biochem Pharmacol. 2024 Dec;230(Pt 1):116551. doi: 10.1016/j.bcp.2024.116551. Epub 2024 Sep 20. PMID: 39307317. 4: Hyeon GE, Eom YB. Totarol exhibits antibacterial effects through antibiofilm and combined interaction against vancomycin-resistant Enterococcus faecalis. Can J Microbiol. 2024 Oct 1;70(10):426-432. doi: 10.1139/cjm-2024-0014. Epub 2024 Jul 24. PMID: 39058360. 5: Haidar S, Amesty Á, Oramas-Royo S, Götz C, El-Awaad E, Kaiser J, Bödecker S, Arnold A, Aichele D, Amaro-Luis JM, Estévez-Braun A, Jose J. 1,2,3-Triazole- totarol conjugates as potent PIP5K1α lipid kinase inhibitors. Bioorg Med Chem. 2024 May 1;105:117727. doi: 10.1016/j.bmc.2024.117727. Epub 2024 Apr 23. PMID: 38669736. 6: Belahcene S, Kebsa W, Akingbade TV, Umar HI, Omoboyowa DA, Alshihri AA, Abo Mansour A, Alhasaniah AH, Oraig MA, Bakkour Y, Leghouchi E. Chemical Composition Antioxidant and Anti-Inflammatory Activities of Myrtus communis L. Leaf Extract: Forecasting ADMET Profiling and Anti-Inflammatory Targets Using Molecular Docking Tools. Molecules. 2024 Feb 14;29(4):849. doi: 10.3390/molecules29040849. PMID: 38398601; PMCID: PMC10893115. 7: Han X, Sharma N, Xu Z, Krajewski S, Li P, Spintzyk S, Lv L, Zhou Y, Thieringer FM, Rupp F. A balance of biocompatibility and antibacterial capability of 3D printed PEEK implants with natural totarol coating. Dent Mater. 2024 Apr;40(4):674-688. doi: 10.1016/j.dental.2024.02.011. Epub 2024 Feb 22. PMID: 38388252. 8: Bhalla P, Chauhan K, Chitme HR, Varshney VK. Phytochemistry and Therapeutic Potential of Cupressus torulosa Needles Essential Oil from India. Chem Biodivers. 2024 Mar;21(3):e202301259. doi: 10.1002/cbdv.202301259. Epub 2024 Feb 21. PMID: 38157454. 9: Boulechfar S, Zellagui A, Bensouici C, Lahouel M, Desdous A. GC-MS based metabolic profile and toxicological evaluation of three Algerian propolis. Nat Prod Res. 2023 Dec 26:1-5. doi: 10.1080/14786419.2023.2298382. Epub ahead of print. PMID: 38146614. 10: Yücel Yücel Y, Servi H, Polatoğlu K, Nalbantsoy A. Anthemis tricolor Containing Unusual Totarol with Cytotoxic and Acetylcholinesterase-Inhibitory Activity. Chem Biodivers. 2024 Feb;21(2):e202300913. doi: 10.1002/cbdv.202300913. Epub 2024 Jan 9. PMID: 38116908. 11: Haroon M, Zahoor AF, Ahmad S, Mansha A, Irfan M, Mushtaq A, Akhtar R, Irfan A, Kotwica-Mojzych K, Mojzych M. The Corey-Seebach Reagent in the 21st Century: A Review. Molecules. 2023 May 26;28(11):4367. doi: 10.3390/molecules28114367. PMID: 37298842; PMCID: PMC10254450. 12: Sultana A, Zare M, Luo H, Ramakrishna S. Surface Engineering Strategies to Enhance the In Situ Performance of Medical Devices Including Atomic Scale Engineering. Int J Mol Sci. 2021 Oct 30;22(21):11788. doi: 10.3390/ijms222111788. PMID: 34769219; PMCID: PMC8583812. 13: Kim C, Le D, Lee M. Diterpenoids Isolated from Podocarpus macrophyllus Inhibited the Inflammatory Mediators in LPS-Induced HT-29 and RAW 264.7 Cells. Molecules. 2021 Jul 17;26(14):4326. doi: 10.3390/molecules26144326. PMID: 34299601; PMCID: PMC8307039. 14: Laamari Y, Oubella A, Bimoussa A, El Mansouri AE, Ketatni EM, Mentre O, Ait Itto MY, Morjani H, Khouili M, Auhmani A. Design, Hemiysnthesis, crystal structure and anticancer activity of 1, 2, 3-triazoles derivatives of totarol. Bioorg Chem. 2021 Oct;115:105165. doi: 10.1016/j.bioorg.2021.105165. Epub 2021 Jul 14. PMID: 34298240. 15: Ribeiro VP, Arruda C, Aldana-Mejia JA, Bastos JK, Tripathi SK, Khan SI, Khan IA, Ali Z. Phytochemical, Antiplasmodial, Cytotoxic and Antimicrobial Evaluation of a Southeast Brazilian Brown Propolis Produced by Apis mellifera Bees. Chem Biodivers. 2021 Sep;18(9):e2100288. doi: 10.1002/cbdv.202100288. Epub 2021 Jul 20. PMID: 34227213. 16: Xu T, Huang L, Liu Z, Ma D, Zhang G, Ning X, Lu X, Liu H, Jiang B. 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. J BUON. 2021 Mar-Apr;26(2):640. PMID: 34077024. 17: Ma LT, Wang CH, Hon CY, Lee YR, Chu FH. Discovery and characterization of diterpene synthases in Chamaecyparis formosensis Matsum. which participated in an unprecedented diterpenoid biosynthesis route in conifer. Plant Sci. 2021 Mar;304:110790. doi: 10.1016/j.plantsci.2020.110790. Epub 2020 Dec 9. PMID: 33568294. 18: Zhao J, Jin X, Wang X, Yang C, Piao X, Kaw HY, Li D. A fast and selective gas liquid microextraction of semiochemicals for quantitative analysis in plants. Plant Sci. 2020 Sep;298:110576. doi: 10.1016/j.plantsci.2020.110576. Epub 2020 Jun 23. PMID: 32771138. 19: Xu Z, Krajewski S, Weindl T, Loeffler R, Li P, Han X, Geis-Gerstorfer J, Wendel HP, Scheideler L, Rupp F. Application of totarol as natural antibacterial coating on dental implants for prevention of peri-implantitis. Mater Sci Eng C Mater Biol Appl. 2020 May;110:110701. doi: 10.1016/j.msec.2020.110701. Epub 2020 Jan 28. PMID: 32204015. 20: Xu T, Huang L, Liu Z, Ma D, Zhang G, Ning X, Lu X, Liu H, Jiang B. 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. J BUON. 2019 Mar-Apr;24(2):686-692. Retraction in: J BUON. 2021 Mar-Apr;26(2):640. PMID: 31128024.