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MedKoo Cat#: 145795 | Name: Ferulenol

Description:

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

Ferulenol is a naturally occurring compound classified as a phenolic compound, derived from plants. It is a member of the ferulic acid family and is known for its potential antioxidant, anti-inflammatory, and antimicrobial properties. Ferulenol has been studied for its biological activities, which may contribute to the health benefits attributed to plants that contain it.

Chemical Structure

Ferulenol
Ferulenol
CAS#6805-34-1

Theoretical Analysis

MedKoo Cat#: 145795

Name: Ferulenol

CAS#: 6805-34-1

Chemical Formula: C24H30O3

Exact Mass: 366.2200

Molecular Weight: 366.50

Elemental Analysis: C, 78.65; H, 8.25; O, 13.10

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Ferulenol; NSC655150; NSC-655150; NSC 655150;
IUPAC/Chemical Name
4-hydroxy-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)-2H-chromen-2-one
InChi Key
NJJDBBUWWOAOLD-CFBAGHHKSA-N
InChi Code
1S/C24H30O3/c1-17(2)9-7-10-18(3)11-8-12-19(4)15-16-21-23(25)20-13-5-6-14-22(20)27-24(21)26/h5-6,9,11,13-15,25H,7-8,10,12,16H2,1-4H3/b18-11+,19-15+
SMILES Code
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC1=C(O)C2=C(OC1=O)C=CC=C2
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 366.50 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: Lahouel M, Zini R, Zellagui A, Rhouati S, Carrupt PA, Morin D. Ferulenol specifically inhibits succinate ubiquinone reductase at the level of the ubiquinone cycle. Biochem Biophys Res Commun. 2007 Mar 30;355(1):252-7. doi: 10.1016/j.bbrc.2007.01.145. Epub 2007 Feb 2. PMID: 17292330. 2: Klamrak A, Nabnueangsap J, Puthongking P, Nualkaew N. Synthesis of Ferulenol by Engineered Escherichia coli: Structural Elucidation by Using the In Silico Tools. Molecules. 2021 Oct 16;26(20):6264. doi: 10.3390/molecules26206264. PMID: 34684845; PMCID: PMC8537342. 3: Lariche N, Lahouel M, Benguedouar L, Zellagui A. Ferulenol, a Sesquiterpene Coumarin, Induce Apoptosis via Mitochondrial Dysregulation in Lung Cancer Induced by Benzo[a]pyrene: Involvement of Bcl2 Protein. Anticancer Agents Med Chem. 2017;17(10):1357-1362. doi: 10.2174/1871520617666170213143444. PMID: 28270083. 4: Kabongo AT, Acharjee R, Sakura T, Bundutidi GM, Hartuti ED, Davies C, Gundogdu O, Kita K, Shiba T, Inaoka DK. Biochemical characterization and identification of ferulenol and embelin as potent inhibitors of malate:quinone oxidoreductase from Campylobacter jejuni. Front Mol Biosci. 2023 Jan 26;10:1095026. doi: 10.3389/fmolb.2023.1095026. PMID: 36776743; PMCID: PMC9908594. 5: Gault G, Lefebvre S, Benoit E, Lattard V, Grancher D. Variability of ferulenol and ferprenin concentration in French giant fennel (Ferula sp.) leaves. Toxicon. 2019 Jul;165:47-55. doi: 10.1016/j.toxicon.2019.04.010. Epub 2019 Apr 26. PMID: 31034847. 6: Tligui N, Ruth GR, Felice LJ. Plasma ferulenol concentration and activity of clotting factors in sheep with Ferula communis variety brevifolia intoxication. Am J Vet Res. 1994 Nov;55(11):1564-9. PMID: 7879980. 7: Monti M, Pinotti M, Appendino G, Dallocchio F, Bellini T, Antognoni F, Poli F, Bernardi F. Characterization of anti-coagulant properties of prenylated coumarin ferulenol. Biochim Biophys Acta. 2007 Oct;1770(10):1437-40. doi: 10.1016/j.bbagen.2007.06.013. Epub 2007 Jul 12. PMID: 17693024. 8: Shiba T, Inaoka DK, Takahashi G, Tsuge C, Kido Y, Young L, Ueda S, Balogun EO, Nara T, Honma T, Tanaka A, Inoue M, Saimoto H, Harada S, Moore AL, Kita K. Insights into the ubiquinol/dioxygen binding and proton relay pathways of the alternative oxidase. Biochim Biophys Acta Bioenerg. 2019 May 1;1860(5):375-382. doi: 10.1016/j.bbabio.2019.03.008. Epub 2019 Mar 22. PMID: 30910528. 9: Louvet MS, Gault G, Lefebvre S, Popowycz F, Boulven M, Besse S, Benoit E, Lattard V, Grancher D. Comparative inhibitory effect of prenylated coumarins, ferulenol and ferprenin, contained in the 'poisonous chemotype' of Ferula communis on mammal liver microsomal VKORC1 activity. Phytochemistry. 2015 Oct;118:124-30. doi: 10.1016/j.phytochem.2015.08.012. Epub 2015 Aug 24. PMID: 26314757. 10: Bocca C, Gabriel L, Bozzo F, Miglietta A. Microtubule-interacting activity and cytotoxicity of the prenylated coumarin ferulenol. Planta Med. 2002 Dec;68(12):1135-7. doi: 10.1055/s-2002-36342. PMID: 12494346. 11: Nadia BH, Wided K, Kheira B, Hassiba R, Lamia B, Rhouati S, Alyane M, Zellagui A, Lahouel M. Disruption of mitochondrial membrane potential by ferulenol and restoration by propolis extract: antiapoptotic role of propolis. Acta Biol Hung. 2009 Dec;60(4):385-98. doi: 10.1556/ABiol.60.2009.4.5. PMID: 20015830. 12: Acharjee R, Talaam KK, Hartuti ED, Matsuo Y, Sakura T, Gloria BM, Hidano S, Kido Y, Mori M, Shiomi K, Sekijima M, Nozaki T, Umeda K, Nishikawa Y, Hamano S, Kita K, Inaoka DK. Biochemical Studies of Mitochondrial Malate: Quinone Oxidoreductase from Toxoplasma gondii. Int J Mol Sci. 2021 Jul 22;22(15):7830. doi: 10.3390/ijms22157830. PMID: 34360597; PMCID: PMC8345934. 13: Sato D, Hartuti ED, Inaoka DK, Sakura T, Amalia E, Nagahama M, Yoshioka Y, Tsuji N, Nozaki T, Kita K, Harada S, Matsubayashi M, Shiba T. Structural and Biochemical Features of Eimeria tenella Dihydroorotate Dehydrogenase, a Potential Drug Target. Genes (Basel). 2020 Dec 7;11(12):1468. doi: 10.3390/genes11121468. PMID: 33297567; PMCID: PMC7762340. 14: Maiuolo J, Musolino V, Guarnieri L, Macrì R, Coppoletta AR, Cardamone A, Serra M, Gliozzi M, Bava I, Lupia C, Tucci L, Bombardelli E, Mollace V. Ferula communis L. (Apiaceae) Root Acetone-Water Extract: Phytochemical Analysis, Cytotoxicity and In Vitro Evaluation of Estrogenic Properties. Plants (Basel). 2022 Jul 22;11(15):1905. doi: 10.3390/plants11151905. PMID: 35893609; PMCID: PMC9329896. 15: Hartuti ED, Inaoka DK, Komatsuya K, Miyazaki Y, Miller RJ, Xinying W, Sadikin M, Prabandari EE, Waluyo D, Kuroda M, Amalia E, Matsuo Y, Nugroho NB, Saimoto H, Pramisandi A, Watanabe YI, Mori M, Shiomi K, Balogun EO, Shiba T, Harada S, Nozaki T, Kita K. Biochemical studies of membrane bound Plasmodium falciparum mitochondrial L-malate:quinone oxidoreductase, a potential drug target. Biochim Biophys Acta Bioenerg. 2018 Mar;1859(3):191-200. doi: 10.1016/j.bbabio.2017.12.004. Epub 2017 Dec 18. PMID: 29269266. 16: Gómez-Canela C, Barata C, Lacorte S. Occurrence, elimination, and risk of anticoagulant rodenticides and drugs during wastewater treatment. Environ Sci Pollut Res Int. 2014;21(11):7194-203. doi: 10.1007/s11356-014-2714-1. Epub 2014 Mar 14. PMID: 24622989. 17: Fraigui O, Lamnaouer D, Faouzi MY. Acute toxicity of ferulenol, a 4-hydroxycoumarin isolated from Ferula communis L. Vet Hum Toxicol. 2002 Feb;44(1):5-7. PMID: 11828999. 18: Hosoya T, Tsuchiya I, Ohta T, Benhanifia M, Kumazawa S. Composition of Algerian Propolis, Plant Origin, and Its Antiangiogenic Activity In Vitro. Molecules. 2021 Oct 28;26(21):6510. doi: 10.3390/molecules26216510. PMID: 34770923; PMCID: PMC8587774. 19: Huang LS, Lümmen P, Berry EA. Crystallographic investigation of the ubiquinone binding site of respiratory Complex II and its inhibitors. Biochim Biophys Acta Proteins Proteom. 2021 Sep;1869(9):140679. doi: 10.1016/j.bbapap.2021.140679. Epub 2021 Jun 3. PMID: 34089891; PMCID: PMC8516616. 20: Appendino G, Mercalli E, Fuzzati N, Arnoldi L, Stavri M, Gibbons S, Ballero M, Maxia A. Antimycobacterial coumarins from the sardinian giant fennel (Ferula communis). J Nat Prod. 2004 Dec;67(12):2108-10. doi: 10.1021/np049706n. PMID: 15620264.

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