MedKoo Cat#: 146155 | Name: Cubebol

Description:

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

Cubebol is a natural sesquiterpene compound found in the essential oil of cubeb berries (Piper cubeba), a plant used in traditional medicine. It exhibits antimicrobial, anti-inflammatory, and antioxidant properties, making it useful in both therapeutic and cosmetic applications. The mechanism of cubebol involves interacting with cellular pathways to reduce oxidative stress and modulate inflammatory responses, offering protection against infections and tissue damage. Cubebol is primarily applied in the production of perfumes, as well as in natural remedies for respiratory and digestive ailments.

Chemical Structure

Cubebol
Cubebol
CAS#23445-02-5

Theoretical Analysis

MedKoo Cat#: 146155

Name: Cubebol

CAS#: 23445-02-5

Chemical Formula: C15H26O

Exact Mass: 222.1984

Molecular Weight: 222.37

Elemental Analysis: C, 81.02; H, 11.79; O, 7.19

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Cubebol;
IUPAC/Chemical Name
(3S,3aR,3bR,4S,7R,7aR)-4-isopropyl-3,7-dimethyloctahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol
InChi Key
KONGRWVLXLWGDV-BYGOPZEFSA-N
InChi Code
1S/C15H26O/c1-9(2)11-6-5-10(3)15-8-7-14(4,16)13(15)12(11)15/h9-13,16H,5-8H2,1-4H3/t10-,11+,12-,13+,14+,15-/m1/s1
SMILES Code
CC(C)[C@@H]1CC[C@@H](C)[C@@]23CC[C@](C)(O)[C@@H]2[C@@H]13
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 222.37 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
1: Chen SC, Jiang BC, Lu YJ, Chang CH, Wu TH, Lin SW, Yin HW, Lee TH, Hsu CH. Characterization and Crystal Structures of a Cubebol-Producing Sesquiterpene Synthase from Antrodia cinnamomea. J Agric Food Chem. 2023 Sep 6;71(35):13014-13023. doi: 10.1021/acs.jafc.3c00570. Epub 2023 Aug 11. PMID: 37566786. 2: Whitehead JN, Leferink NGH, Komati Reddy G, Levy CW, Hay S, Takano E, Scrutton NS. How a 10-epi-Cubebol Synthase Avoids Premature Reaction Quenching to Form a Tricyclic Product at High Purity. ACS Catal. 2022 Oct 7;12(19):12123-12131. doi: 10.1021/acscatal.2c03155. Epub 2022 Sep 21. PMID: 36249875; PMCID: PMC9552170. 3: Rabe P, Dickschat JS. The EIMS fragmentation mechanisms of the sesquiterpenes corvol ethers A and B, epi-cubebol and isodauc-8-en-11-ol. Beilstein J Org Chem. 2016 Jul 5;12:1380-94. doi: 10.3762/bjoc.12.132. PMID: 27559388; PMCID: PMC4979868. 4: Schäfer E, Seibold PS, Bartram S, Trottmann F, Haensch VG, Gressler M, Chadeayne AR, Hertweck C, O'Connor SE, Hoffmeister D. A "Magic Mushroom" Multi- Product Sesquiterpene Synthase. Chembiochem. 2023 Nov 2;24(21):e202300511. doi: 10.1002/cbic.202300511. Epub 2023 Sep 12. PMID: 37614035. 5: Fehr C, Galindo J. Synthesis of (-)-cubebol by face-selective platinum-, gold-, or copper-catalyzed cycloisomerization: evidence for chirality transfer. Angew Chem Int Ed Engl. 2006 Apr 28;45(18):2901-4. doi: 10.1002/anie.200504543. PMID: 16555348. 6: Mischko W, Hirte M, Fuchs M, Mehlmer N, Brück TB. Identification of sesquiterpene synthases from the Basidiomycota Coniophora puteana for the efficient and highly selective β-copaene and cubebol production in E. coli. Microb Cell Fact. 2018 Oct 22;17(1):164. doi: 10.1186/s12934-018-1010-z. PMID: 30348159; PMCID: PMC6198442. 7: Fehr C, Winter B, Magpantay I. Synthesis of (-)-cubebol by face-selective platinum-, gold-, or copper-catalyzed cycloisomerization: evidence of chirality transfer and mechanistic insights. Chemistry. 2009 Sep 28;15(38):9773-84. doi: 10.1002/chem.200901292. PMID: 19691071. 8: Hodgson DM, Salik S, Fox DJ. Stereocontrolled syntheses of (-)-cubebol and (-)-10-epicubebol involving intramolecular cyclopropanation of alpha-lithiated epoxides. J Org Chem. 2010 Apr 2;75(7):2157-68. doi: 10.1021/jo9022974. PMID: 20063852. 9: Asadollahi MA, Maury J, Schalk M, Clark A, Nielsen J. Enhancement of farnesyl diphosphate pool as direct precursor of sesquiterpenes through metabolic engineering of the mevalonate pathway in Saccharomyces cerevisiae. Biotechnol Bioeng. 2010 May 1;106(1):86-96. doi: 10.1002/bit.22668. PMID: 20091767. 10: Fürstner A, Hannen P. Platinum- and gold-catalyzed rearrangement reactions of propargyl acetates: total syntheses of (-)-alpha-cubebene, (-)-cubebol, sesquicarene and related terpenes. Chemistry. 2006 Apr 3;12(11):3006-19. doi: 10.1002/chem.200501299. PMID: 16456909. 11: Saldivar EV, Ding Y, Poretsky E, Bird S, Block AK, Huffaker A, Schmelz EA. Maize Terpene Synthase 8 (ZmTPS8) Contributes to a Complex Blend of Fungal- Elicited Antibiotics. Plants (Basel). 2023 Mar 1;12(5):1111. doi: 10.3390/plants12051111. PMID: 36903970; PMCID: PMC10005556. 12: Jung Y, Mitsuhashi T, Kikuchi T, Fujita M. Functional Plasticity of a Viral Terpene Synthase, OILTS, that Shows Non-Specific Metal Cofactor Binding and Metal-Dependent Biosynthesis. Chemistry. 2024 Jun 3;30(31):e202304317. doi: 10.1002/chem.202304317. Epub 2024 Apr 18. PMID: 38527951. 13: LeGay CM, Gorobets E, Iftinca M, Ramachandran R, Altier C, Derksen DJ. Natural-Product-Derived Transient Receptor Potential Melastatin 8 (TRPM8) Channel Modulators. Org Lett. 2016 Jun 3;18(11):2746-9. doi: 10.1021/acs.orglett.6b01222. Epub 2016 May 12. PMID: 27171974. 14: Basile S, Badalamenti N, Riccobono O, Guarino S, Ilardi V, Bruno M, Peri E. Chemical Composition and Evaluation of Insecticidal Activity of Calendula incana subsp. maritima and Laserpitium siler subsp. siculum Essential Oils against Stored Products Pests. Molecules. 2022 Jan 18;27(3):588. doi: 10.3390/molecules27030588. PMID: 35163853; PMCID: PMC8840456. 15: Fadel H, Benayache F, Chalchat JC, Figueredo G, Chalard P, Hazmoune H, Benayache S. Essential oil constituents of Juniperus oxycedrus L. and Cupressus sempervirens L. (Cupressaceae) growing in Aures region of Algeria. Nat Prod Res. 2021 Aug;35(15):2616-2620. doi: 10.1080/14786419.2019.1687473. Epub 2019 Nov 7. PMID: 31696737. 16: Gu HJ, Cheng SS, Huang CG, Chen WJ, Chang ST. Mosquito larvicidal activities of extractives from black heartwood-type Cryptomeria japonica. Parasitol Res. 2009 Oct;105(5):1455-8. doi: 10.1007/s00436-009-1550-6. Epub 2009 Jul 3. PMID: 19575217. 17: Asadollahi MA, Maury J, Patil KR, Schalk M, Clark A, Nielsen J. Enhancing sesquiterpene production in Saccharomyces cerevisiae through in silico driven metabolic engineering. Metab Eng. 2009 Nov;11(6):328-34. doi: 10.1016/j.ymben.2009.07.001. Epub 2009 Jul 18. PMID: 19619667. 18: Bains A, Sridhar K, Kaushik R, Chawla P, Sharma M. Enzyme-assisted polysaccharides extraction from Calocybe indica: Synergistic antibiofilm and oxidative stability of essential oil nanoemulsion. Int J Biol Macromol. 2023 Jul 1;242(Pt 2):124843. doi: 10.1016/j.ijbiomac.2023.124843. Epub 2023 May 13. PMID: 37182620. 19: T R, Sharma D, Lin F, Choong YK, Lim C, Jobichen C, Zhang C. Structural Understanding of Fungal Terpene Synthases for the Formation of Linear or Cyclic Terpene Products. ACS Catal. 2023 Mar 27;13(7):4949-4959. doi: 10.1021/acscatal.2c05598. PMID: 37066048; PMCID: PMC10088877. 20: Jiang Y, Huang D, Lu C, Ye S, Li L, Li T, Liu X, Chen B, Guo J, Lu L. Shorten spreading duration enhance the quality of summer Meitan Cuiya tea. Food Chem X. 2024 Oct 5;24:101878. doi: 10.1016/j.fochx.2024.101878. PMID: 39493592; PMCID: PMC11528227.