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MedKoo Cat#: 558062 | Name: Levomenol
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Description:

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

Levomenol is found in fats and oils.

Chemical Structure

Levomenol
CAS#23089-26-1

Theoretical Analysis

MedKoo Cat#: 558062

Name: Levomenol

CAS#: 23089-26-1

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

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (S-(theta,theta))-; (-)-6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol;
IUPAC/Chemical Name
3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (alphaS,1S)-
InChi Key
RGZSQWQPBWRIAQ-CABCVRRESA-N
InChi Code
InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1
SMILES Code
O[C@](CC/C=C(C)\C)(C)[C@@H]1CC=C(C)CC1
Appearance
Liquid
Purity
>90% (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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levomenol ((-)-α-Bisabolol), a monocyclic sesquiterpene alcohol, exerts antioxidant, anti-inflammatory, and anti-apoptotic activities.
In vitro activity:
α-Bisabolol significantly decreased the expression of proinflammatory chemokines (CXCL-1 and IL-8) mRNA in HT-29 cells treated with TNF-α and HT-29 PPAR-γ promoter activity. These results demonstrate that α-bisabolol mitigates colonic inflammation by inhibiting MAPK signaling and stimulating PPAR-γ expression. Reference: PPAR Res. 2022 Apr 13;2022:5498115. https://pubmed.ncbi.nlm.nih.gov/35465355/
In vivo activity:
Mice were treated with (-)-α-bisabolol (50, 100 and 200 mg/kg/day, orally) or vehicle (3% tween 80) one day before and 1 h after pMCAO and the treatment continued once daily for the following five days. (-)-α-bisabolol increased the locomotor activity which was reduced by cerebral ischemia and improved pMCAO-induced working, spatial, object recognition, and aversive memories deficits. (-)-α-bisabolol (200 mg/kg) significantly prevented the increase of myeloperoxidase (MPO) activity, TNF-α immunoreactivity in the temporal cortex, and the increase of iNOS both in the temporal cortex and in the striatum. Reference: Eur J Pharmacol. 2019 Jan 5;842:270-280. https://pubmed.ncbi.nlm.nih.gov/30287152/
Solvent mg/mL mM comments
Solubility
DMSO 100.0 449.70
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 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
Formulation protocol:
1. Venkataraman B, Almarzooqi S, Raj V, Dudeja PK, Bhongade BA, Patil RB, Ojha SK, Attoub S, Adrian TE, Subramanya SB. α-Bisabolol Mitigates Colon Inflammation by Stimulating Colon PPAR-γ Transcription Factor: In Vivo and In Vitro Study. PPAR Res. 2022 Apr 13;2022:5498115. doi: 10.1155/2022/5498115. PMID: 35465355; PMCID: PMC9020997. 2. Laws Iii JS, Shrestha S, Smid SD. Cannabis terpenes display variable protective and anti-aggregatory actions against neurotoxic β amyloid in vitro: highlighting the protective bioactivity of α-bisabolol in motorneuronal-like NSC-34 cells. Neurotoxicology. 2022 May;90:81-87. doi: 10.1016/j.neuro.2022.03.001. Epub 2022 Mar 10. PMID: 35278524. 3. Melo LT, Panchalingam V, Cherkas P, Campos AR, Avivi-Arber L, Sessle BJ. (-)-α-Bisabolol reduces nociception and trigeminal central sensitisation in acute orofacial neuropathic pain induced by infraorbital nerve injury. Life Sci. 2019 Jun 15;227:122-128. doi: 10.1016/j.lfs.2019.04.032. Epub 2019 Apr 16. PMID: 31002923. 4. Fernandes MYD, Carmo MRSD, Fonteles AA, Neves JCS, Silva ATAD, Pereira JF, Ferreira EO, Lima NMR, Neves KRT, Andrade GM. (-)-α-bisabolol prevents neuronal damage and memory deficits through reduction of proinflammatory markers induced by permanent focal cerebral ischemia in mice. Eur J Pharmacol. 2019 Jan 5;842:270-280. doi: 10.1016/j.ejphar.2018.09.036. Epub 2018 Oct 1. PMID: 30287152.
In vitro protocol:
1. Venkataraman B, Almarzooqi S, Raj V, Dudeja PK, Bhongade BA, Patil RB, Ojha SK, Attoub S, Adrian TE, Subramanya SB. α-Bisabolol Mitigates Colon Inflammation by Stimulating Colon PPAR-γ Transcription Factor: In Vivo and In Vitro Study. PPAR Res. 2022 Apr 13;2022:5498115. doi: 10.1155/2022/5498115. PMID: 35465355; PMCID: PMC9020997. 2. Laws Iii JS, Shrestha S, Smid SD. Cannabis terpenes display variable protective and anti-aggregatory actions against neurotoxic β amyloid in vitro: highlighting the protective bioactivity of α-bisabolol in motorneuronal-like NSC-34 cells. Neurotoxicology. 2022 May;90:81-87. doi: 10.1016/j.neuro.2022.03.001. Epub 2022 Mar 10. PMID: 35278524.
In vivo protocol:
1. Melo LT, Panchalingam V, Cherkas P, Campos AR, Avivi-Arber L, Sessle BJ. (-)-α-Bisabolol reduces nociception and trigeminal central sensitisation in acute orofacial neuropathic pain induced by infraorbital nerve injury. Life Sci. 2019 Jun 15;227:122-128. doi: 10.1016/j.lfs.2019.04.032. Epub 2019 Apr 16. PMID: 31002923. 2. Fernandes MYD, Carmo MRSD, Fonteles AA, Neves JCS, Silva ATAD, Pereira JF, Ferreira EO, Lima NMR, Neves KRT, Andrade GM. (-)-α-bisabolol prevents neuronal damage and memory deficits through reduction of proinflammatory markers induced by permanent focal cerebral ischemia in mice. Eur J Pharmacol. 2019 Jan 5;842:270-280. doi: 10.1016/j.ejphar.2018.09.036. Epub 2018 Oct 1. PMID: 30287152.
1: Arenberger P, Arenbergerová M, Drozenová H, Hladíková M, Holcová S. Effect of topical heparin and levomenol on atopic dermatitis: a randomized four-arm, placebo-controlled, double-blind clinical study. J Eur Acad Dermatol Venereol. 2011 Jun;25(6):688-94. doi: 10.1111/j.1468-3083.2010.03950.x. Epub 2011 Jan 9. PubMed PMID: 21214633. 2: Hahn B, Hölzl J. [Absorption, distribution and metabolism of [14C]-levomenol in the skin]. Arzneimittelforschung. 1987 Jun;37(6):716-20. German. PubMed PMID: 3663271. 3: Maurya AK, Singh M, Dubey V, Srivastava S, Luqman S, Bawankule DU. α-(-)-bisabolol reduces pro-inflammatory cytokine production and ameliorates skin inflammation. Curr Pharm Biotechnol. 2014;15(2):173-81. PubMed PMID: 24894548. 4: Han GH, Kim SK, Yoon PK, Kang Y, Kim BS, Fu Y, Sung BH, Jung HC, Lee DH, Kim SW, Lee SG. Fermentative production and direct extraction of (-)-α-bisabolol in metabolically engineered Escherichia coli. Microb Cell Fact. 2016 Nov 8;15(1):185. Erratum in: Microb Cell Fact. 2017 Jan 31;16(1):19. PubMed PMID: 27825357; PubMed Central PMCID: PMC5101696. 5: Karami A, Dehghan-Mashtani N. Composition of the essential oil of Stachys benthamiana Boiss. from the south of Iran. Nat Prod Res. 2015;29(15):1473-6. doi: 10.1080/14786419.2014.1003185. Epub 2015 Jan 21. PubMed PMID: 25605295. 6: Crocco EI, Veasey JV, Boin MF, Lellis RF, Alves RO. A novel cream formulation containing nicotinamide 4%, arbutin 3%, bisabolol 1%, and retinaldehyde 0.05% for treatment of epidermal melasma. Cutis. 2015 Nov;96(5):337-42. PubMed PMID: 26682557. 7: Frikeche J, Couteau C, Roussakis C, Coiffard LJ. Research on the immunosuppressive activity of ingredients contained in sunscreens. Arch Dermatol Res. 2015 Apr;307(3):211-8. doi: 10.1007/s00403-014-1528-9. Epub 2015 Jan 4. PubMed PMID: 25556843. 8: Rottini MM, Amaral AC, Ferreira JL, Silva JR, Taniwaki NN, Souza Cda S, d'Escoffier LN, Almeida-Souza F, Hardoim Dde J, Gonçalves da Costa SC, Calabrese Kda S. In vitro evaluation of (-)α-bisabolol as a promising agent against Leishmania amazonensis. Exp Parasitol. 2015 Jan;148:66-72. doi: 10.1016/j.exppara.2014.10.001. Epub 2014 Nov 5. PubMed PMID: 25448354. 9: Nurulain S, Prytkova T, Sultan AM, Ievglevskyi O, Lorke D, Yang KH, Petroianu G, Howarth FC, Kabbani N, Oz M. Inhibitory actions of bisabolol on α7-nicotinic acetylcholine receptors. Neuroscience. 2015 Oct 15;306:91-9. doi: 10.1016/j.neuroscience.2015.08.019. Epub 2015 Aug 15. PubMed PMID: 26283025. 10: Corpas-López V, Morillas-Márquez F, Navarro-Moll MC, Merino-Espinosa G, Díaz-Sáez V, Martín-Sánchez J. (-)-α-Bisabolol, a Promising Oral Compound for the Treatment of Visceral Leishmaniasis. J Nat Prod. 2015 Jun 26;78(6):1202-7. doi: 10.1021/np5008697. Epub 2015 Jun 15. PubMed PMID: 26076227. 11: Romagnoli C, Baldisserotto A, Malisardi G, Vicentini CB, Mares D, Andreotti E, Vertuani S, Manfredini S. A Multi-Target Approach toward the Development of Novel Candidates for Antidermatophytic Activity: Ultrastructural Evidence on α-Bisabolol-Treated Microsporum gypseum. Molecules. 2015 Jun 26;20(7):11765-76. doi: 10.3390/molecules200711765. PubMed PMID: 26132903. 12: Leong HJ, Jang I, Hyun KS, Jung SK, Hong GH, Jeong HA, Oh SG. Preparation of alpha-bisabolol and phenylethyl resorcinol/TiO2 hybrid composites for potential applications in cosmetics. Int J Cosmet Sci. 2016 Oct;38(5):524-34. doi: 10.1111/ics.12339. Epub 2016 Jun 2. PubMed PMID: 27139639. 13: Corpas-López V, Merino-Espinosa G, López-Viota M, Gijón-Robles P, Morillas-Mancilla MJ, López-Viota J, Díaz-Sáez V, Morillas-Márquez F, Navarro Moll MC, Martín-Sánchez J. Topical Treatment of Leishmania tropica Infection Using (-)-α-Bisabolol Ointment in a Hamster Model: Effectiveness and Safety Assessment. J Nat Prod. 2016 Sep 23;79(9):2403-7. doi: 10.1021/acs.jnatprod.6b00740. Epub 2016 Sep 12. PubMed PMID: 27616730. 14: Sieniawska E, Swatko-Ossor M, Sawicki R, Ginalska G. Morphological Changes in the Overall Mycobacterium tuberculosis H37Ra Cell Shape and Cytoplasm Homogeneity due to Mutellina purpurea L. Essential Oil and Its Main Constituents. Med Princ Pract. 2015;24(6):527-32. doi: 10.1159/000439351. Epub 2015 Sep 19. PubMed PMID: 26381133; PubMed Central PMCID: PMC5588283. 15: Sampaio TL, Menezes RR, da Costa MF, Meneses GC, Arrieta MC, Chaves Filho AJ, de Morais GB, Libório AB, Alves RS, Evangelista JS, Martins AM. Nephroprotective effects of (-)-α-bisabolol against ischemic-reperfusion acute kidney injury. Phytomedicine. 2016 Dec 15;23(14):1843-1852. doi: 10.1016/j.phymed.2016.11.008. Epub 2016 Nov 11. PubMed PMID: 27912887. 16: Barreto RSS, Quintans JSS, Amarante RKL, Nascimento TS, Amarante RS, Barreto AS, Pereira EWM, Duarte MC, Coutinho HDM, Menezes IRA, Zengin G, Aktumsek A, Quintans-Júnior LJ. Evidence for the involvement of TNF-α and IL-1β in the antinociceptive and anti-inflammatory activity of Stachys lavandulifolia Vahl. (Lamiaceae) essential oil and (-)-α-bisabolol, its main compound, in mice. J Ethnopharmacol. 2016 Sep 15;191:9-18. doi: 10.1016/j.jep.2016.06.022. Epub 2016 Jun 9. PubMed PMID: 27292196. 17: Rigo A, Vinante F. The antineoplastic agent α-bisabolol promotes cell death by inducing pores in mitochondria and lysosomes. Apoptosis. 2016 Aug;21(8):917-27. doi: 10.1007/s10495-016-1257-y. PubMed PMID: 27278818. 18: Cerceau CI, Barbosa LCA, Alvarenga ES, Ferreira AG, Thomasi SS. A validated (1)H NMR method for quantitative analysis of α-bisabolol in essential oils of Eremanthus erythropappus. Talanta. 2016 Dec 1;161:71-79. doi: 10.1016/j.talanta.2016.08.032. Epub 2016 Aug 10. PubMed PMID: 27769470. 19: Solovăstru LG, Stîncanu A, De Ascentii A, Capparé G, Mattana P, Vâţă D. Randomized, controlled study of innovative spray formulation containing ozonated oil and α-bisabolol in the topical treatment of chronic venous leg ulcers. Adv Skin Wound Care. 2015 Sep;28(9):406-9. doi: 10.1097/01.ASW.0000470155.29821.ed. PubMed PMID: 26280699. 20: Baldissera MD, Grando TH, de Souza CF, Cossetin LF, da Silva APT, Giongo JL, Monteiro SG. A nanotechnology based new approach for Trypanosoma evansi chemotherapy: In vitro and vivo trypanocidal effect of (-)-α-bisabolol. Exp Parasitol. 2016 Nov;170:156-160. doi: 10.1016/j.exppara.2016.09.018. Epub 2016 Sep 28. PubMed PMID: 27693361.