Kaurene

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

Hodoodo CAT#: H558143

CAS#: 34424-57-2

Description: Kaurene is a tetracyclic diterpene consisting of ent-kaurane, where the 6-methyl group is replaced by methylene.

Chemical Structure

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Kaurene
CAS# 34424-57-2
Instruction

Theoretical Analysis

Hodoodo Cat#: H558143
Name: Kaurene
CAS#: 34424-57-2
Chemical Formula: C20H32
Exact Mass: 272.25
Molecular Weight: 272.480
Elemental Analysis: C, 88.16; H, 11.84

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym:

IUPAC/Chemical Name: (4aR,8S,9S,11aR,11bR)-4,4,8,11b-tetramethyl-3,4,4a,5,6,7,8,9,10,11,11a,11b-dodecahydro-6a,9-methanocyclohepta[a]naphthalene

InChi Key: IODSADAHQKFXES-CCJFMQDPSA-N

InChi Code: InChI=1S/C20H32/c1-14-12-20-11-8-16-18(2,3)9-5-10-19(16,4)17(20)7-6-15(14)13-20/h5,10,14-17H,6-9,11-13H2,1-4H3/t14-,15-,16+,17-,19+,20?/m0/s1

SMILES Code: C[C@H]1CC23CC[C@H]4[C@](C=CCC4(C)C)(C)[C@@H]2CC[C@H]1C3

Appearance: Solid powder

Purity: >98% (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: >2 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 272.48 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:
In vitro protocol:
In vivo protocol:

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1: Kong MK, Kang HJ, Kim JH, Oh SH, Lee PC. Metabolic engineering of the Stevia rebaudiana ent-kaurene biosynthetic pathway in recombinant Escherichia coli. J Biotechnol. 2015 Nov 20;214:95-102. doi: 10.1016/j.jbiotec.2015.09.016. Epub 2015 Sep 21. PubMed PMID: 26392384.

2: Lu X, Hershey DM, Wang L, Bogdanove AJ, Peters RJ. An ent-kaurene-derived diterpenoid virulence factor from Xanthomonas oryzae pv. oryzicola. New Phytol. 2015 Apr;206(1):295-302. doi: 10.1111/nph.13187. Epub 2014 Nov 18. PubMed PMID: 25406717.

3: Bustos-Brito C, Sánchez-Castellanos M, Esquivel B, Calderón JS, Calzada F, Yépez-Mulia L, Joseph-Nathan P, Cuevas G, Quijano L. ent-Kaurene Glycosides from Ageratina cylindrica. J Nat Prod. 2015 Nov 25;78(11):2580-7. doi: 10.1021/acs.jnatprod.5b00488. Epub 2015 Oct 30. PubMed PMID: 26517282.

4: Miyazaki S, Toyoshima H, Natsume M, Nakajima M, Kawaide H. Blue-light irradiation up-regulates the ent-kaurene synthase gene and affects the avoidance response of protonemal growth in Physcomitrella patens. Planta. 2014 Jul;240(1):117-24. doi: 10.1007/s00425-014-2068-4. Epub 2014 Apr 9. PubMed PMID: 24715198.

5: Shimane M, Ueno Y, Morisaki K, Oogami S, Natsume M, Hayashi K, Nozaki H, Kawaide H. Molecular evolution of the substrate specificity of ent-kaurene synthases to adapt to gibberellin biosynthesis in land plants. Biochem J. 2014 Sep 15;462(3):539-46. doi: 10.1042/BJ20140134. PubMed PMID: 24983886.

6: Irmisch S, Müller AT, Schmidt L, Günther J, Gershenzon J, Köllner TG. One amino acid makes the difference: the formation of ent-kaurene and 16α-hydroxy-ent-kaurane by diterpene synthases in poplar. BMC Plant Biol. 2015 Oct 28;15:262. doi: 10.1186/s12870-015-0647-6. PubMed PMID: 26511849; PubMed Central PMCID: PMC4625925.

7: Zhan X, Bach SS, Hansen NL, Lunde C, Simonsen HT. Additional diterpenes from Physcomitrella patens synthesized by copalyl diphosphate/kaurene synthase (PpCPS/KS). Plant Physiol Biochem. 2015 Nov;96:110-4. doi: 10.1016/j.plaphy.2015.07.011. Epub 2015 Jul 17. PubMed PMID: 26248039.

8: Liu W, Feng X, Zheng Y, Huang CH, Nakano C, Hoshino T, Bogue S, Ko TP, Chen CC, Cui Y, Li J, Wang I, Hsu ST, Oldfield E, Guo RT. Structure, function and inhibition of ent-kaurene synthase from Bradyrhizobium japonicum. Sci Rep. 2014 Oct 1;4:6214. doi: 10.1038/srep06214. PubMed PMID: 25269599; PubMed Central PMCID: PMC4180811.

9: Tezuka D, Ito A, Mitsuhashi W, Toyomasu T, Imai R. The rice ent-KAURENE SYNTHASE LIKE 2 encodes a functional ent-beyerene synthase. Biochem Biophys Res Commun. 2015 May 8;460(3):766-71. doi: 10.1016/j.bbrc.2015.03.104. Epub 2015 Mar 28. PubMed PMID: 25824047.

10: Jia M, Peters RJ. Extending a Single Residue Switch for Abbreviating Catalysis in Plant ent-Kaurene Synthases. Front Plant Sci. 2016 Nov 22;7:1765. eCollection 2016. PubMed PMID: 27920791; PubMed Central PMCID: PMC5118566.

11: Su P, Tong Y, Cheng Q, Hu Y, Zhang M, Yang J, Teng Z, Gao W, Huang L. Functional characterization of ent-copalyl diphosphate synthase, kaurene synthase and kaurene oxidase in the Salvia miltiorrhiza gibberellin biosynthetic pathway. Sci Rep. 2016 Mar 14;6:23057. doi: 10.1038/srep23057. PubMed PMID: 26971881; PubMed Central PMCID: PMC4789781.

12: Li L, Chen X, Ma C, Wu H, Qi S. Piriformospora indica requires kaurene synthase activity for successful plant colonization. Plant Physiol Biochem. 2016 May;102:151-60. doi: 10.1016/j.plaphy.2016.02.017. Epub 2016 Feb 16. PubMed PMID: 26943021.

13: Bromann K, Toivari M, Viljanen K, Ruohonen L, Nakari-Setälä T. Engineering Aspergillus nidulans for heterologous ent-kaurene and gamma-terpinene production. Appl Microbiol Biotechnol. 2016 Jul;100(14):6345-59. doi: 10.1007/s00253-016-7517-5. Epub 2016 Apr 20. PubMed PMID: 27098256.

14: Fu J, Ren F, Lu X, Mao H, Xu M, Degenhardt J, Peters RJ, Wang Q. A Tandem Array of ent-Kaurene Synthases in Maize with Roles in Gibberellin and More Specialized Metabolism. Plant Physiol. 2016 Feb;170(2):742-51. doi: 10.1104/pp.15.01727. Epub 2015 Nov 30. PubMed PMID: 26620527; PubMed Central PMCID: PMC4734586.

15: Mafu S, Jia M, Zi J, Morrone D, Wu Y, Xu M, Hillwig ML, Peters RJ. Probing the promiscuity of ent-kaurene oxidases via combinatorial biosynthesis. Proc Natl Acad Sci U S A. 2016 Mar 1;113(9):2526-31. doi: 10.1073/pnas.1512096113. Epub 2016 Feb 16. PubMed PMID: 26884192; PubMed Central PMCID: PMC4780596.

16: Hershey DM, Lu X, Zi J, Peters RJ. Functional conservation of the capacity for ent-kaurene biosynthesis and an associated operon in certain rhizobia. J Bacteriol. 2014 Jan;196(1):100-6. doi: 10.1128/JB.01031-13. Epub 2013 Oct 18. PubMed PMID: 24142247; PubMed Central PMCID: PMC3911121.

17: Zou M, Yu SS, Wang K, Zhang DY, Wu XM, Hua WY. Glycosylation of ent-kaurene derivatives and an evaluation of their cytotoxic activities. Chin J Nat Med. 2013 May;11(3):289-95. doi: 10.1016/S1875-5364(13)60031-X. PubMed PMID: 23725844.

18: Miyazaki S, Katsumata T, Natsume M, Kawaide H. The CYP701B1 of Physcomitrella patens is an ent-kaurene oxidase that resists inhibition by uniconazole-P. FEBS Lett. 2011 Jun 23;585(12):1879-83. doi: 10.1016/j.febslet.2011.04.057. Epub 2011 Apr 30. PubMed PMID: 21545802.

19: Jackson AJ, Hershey DM, Chesnut T, Xu M, Peters RJ. Biochemical characterization of the castor bean ent-kaurene synthase(-like) family supports quantum chemical view of diterpene cyclization. Phytochemistry. 2014 Jul;103:13-21. doi: 10.1016/j.phytochem.2014.04.005. Epub 2014 May 5. PubMed PMID: 24810014; PubMed Central PMCID: PMC4062354.

20: Li D, Xu S, Cai H, Pei L, Zhang H, Wang L, Yao H, Wu X, Jiang J, Sun Y, Xu J. Enmein-type diterpenoid analogs from natural kaurene-type oridonin: Synthesis and their antitumor biological evaluation. Eur J Med Chem. 2013 Jun;64:215-21. doi: 10.1016/j.ejmech.2013.04.012. Epub 2013 Apr 11. PubMed PMID: 23644204.