Rapanone | CAS#573-40-0 | biochemical

MedKoo Cat#: 145799 | Name: Rapanone

Description:

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

Rapanone is a compound that has been studied for its antimicrobial and antifungal properties. It is part of a group of bioactive compounds known for their potential in treating infections caused by bacteria and fungi. Rapanone is of interest mainly in the field of natural product chemistry and pharmacology, where researchers are exploring its ability to disrupt microbial cell functions.

Chemical Structure

Rapanone

CAS#573-40-0

Theoretical Analysis

MedKoo Cat#: 145799

Name: Rapanone

CAS#: 573-40-0

Chemical Formula: C19H30O4

Exact Mass: 322.2100

Molecular Weight: 322.45

Elemental Analysis: C, 70.77; H, 9.38; O, 19.85

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

Rapanone; NSC-340285; NSC340285; NSC 340285; Ropanone;

IUPAC/Chemical Name

2,5-dihydroxy-3-tridecylcyclohexa-2,5-diene-1,4-dione

InChi Key

AMKNOBHCKRZHIO-UHFFFAOYSA-N

InChi Code

1S/C19H30O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(22)16(20)14-17(21)19(15)23/h14,20,23H,2-13H2,1H3

SMILES Code

CCCCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 322.45 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.

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: Pardo Andreu GL, Reis FZD, González-Durruthy M, Hernández RD, D'Vries RF, Vanden Berghe W, Alberici LC. Rapanone, a naturally occurring benzoquinone, inhibits mitochondrial respiration and induces HepG2 cell death. Toxicol In Vitro. 2020 Mar;63:104737. doi: 10.1016/j.tiv.2019.104737. Epub 2019 Nov 20. PMID: 31756542. 2: Wróbel-Biedrawa D, Galanty A, Zagrodzki P, Podolak I. Optimization of Extraction Conditions and Cytotoxic Activity of Rapanone in Comparison to Its Homologue, Embelin. Molecules. 2022 Nov 16;27(22):7912. doi: 10.3390/molecules27227912. PMID: 36432013; PMCID: PMC9693145. 3: Wróbel-Biedrawa D, Grabowska K, Galanty A, Sobolewska D, Żmudzki P, Podolak I. Anti-melanoma potential of two benzoquinone homologues embelin and rapanone - a comparative in vitro study. Toxicol In Vitro. 2020 Jun;65:104826. doi: 10.1016/j.tiv.2020.104826. Epub 2020 Mar 10. PMID: 32169436. 4: de la Vega-Hernández K, Antuch M, Cuesta-Rubio O, Núñez-Figueredo Y, Pardo- Andreu GL. Discerning the antioxidant mechanism of rapanone: A naturally occurring benzoquinone with iron complexing and radical scavenging activities. J Inorg Biochem. 2017 May;170:134-147. doi: 10.1016/j.jinorgbio.2017.02.019. Epub 2017 Feb 20. PMID: 28237732. 5: da Costa RC, Santana DB, Araújo RM, de Paula JE, do Nascimento PC, Lopes NP, Braz-Filho R, Espindola LS. Discovery of the rapanone and suberonone mixture as a motif for leishmanicidal and antifungal applications. Bioorg Med Chem. 2014 Jan 1;22(1):135-40. doi: 10.1016/j.bmc.2013.11.044. Epub 2013 Dec 4. PMID: 24331757. 6: Ospina LF, Calle J, Arteaga L, Pinzón R, Alcaraz MJ, Payá M. Inhibition of acute and chronic inflammatory responses by the hydroxybenzoquinonic derivative rapanone. Planta Med. 2001 Dec;67(9):791-5. doi: 10.1055/s-2001-18839. PMID: 11745012. 7: Arunachalam A, Sankar M, Pandi B, Paul S, Thilagar S. Evaluation of Rapanone and Nectandrin B as novel inhibitors for targeting the metastatic regulator protein BACH1 using breast cancer cell line Mcf-7. J Biomol Struct Dyn. 2024;42(20):11185-11200. doi: 10.1080/07391102.2023.2260880. Epub 2023 Sep 25. PMID: 37747058. 8: Kuete V, Omosa LK, Tala VR, Midiwo JO, Mbaveng AT, Swaleh S, Karaosmanoğlu O, Sivas H. Cytotoxicity of Plumbagin, Rapanone and 12 other naturally occurring Quinones from Kenyan Flora towards human carcinoma cells. BMC Pharmacol Toxicol. 2016 Dec 21;17(1):60. doi: 10.1186/s40360-016-0104-7. PMID: 27998305; PMCID: PMC5175396. 9: Mariyappan V, Munuswamy-Ramanujam G, Ramasamy M. Synthesis of novel rapanone derivatives via organocatalytic reductive C-alkylation: biological evaluation of antioxidant properties, in vivo zebrafish embryo toxicity, and docking studies. RSC Med Chem. 2023 Dec 4;15(2):623-635. doi: 10.1039/d3md00564j. PMID: 38389875; PMCID: PMC10880907. 10: Calle J, Olarte J, Pinzon R, Ospina LF, Mendoza MC, Orozco MJ. Alterations in the reproduction of mice induced by rapanone. J Ethnopharmacol. 2000 Aug;71(3):521-5. doi: 10.1016/s0378-8741(99)00214-7. PMID: 10940592. 11: Ashok E, Lakshmi PR, Sanwal SD, Ramachary DB. High-yielding total synthesis of embelin, rapanone, and irisoquin A, D, F. Org Biomol Chem. 2025 Jan 28. doi: 10.1039/d4ob01706d. Epub ahead of print. PMID: 39873637. 12: Podolak I, Mynarski A, Wróbel D, Grabowska K, Galanty A. Bioactive benzoquinones content variability in red-berry and white-berry varieties of Ardisia crenata Sims. and assessment of cytotoxic activity. Nat Prod Res. 2021 Jan;35(1):157-161. doi: 10.1080/14786419.2019.1614575. Epub 2019 May 28. PMID: 31135229. 13: Morais LS, Dusi RG, Demarque DP, Silva RL, Albernaz LC, Báo SN, Merten C, Antinarelli LMR, Coimbra ES, Espindola LS. Antileishmanial compounds from Connarus suberosus: Metabolomics, isolation and mechanism of action. PLoS One. 2020 Nov 6;15(11):e0241855. doi: 10.1371/journal.pone.0241855. PMID: 33156835; PMCID: PMC7647111. 14: Dallacker F, Löhnert G. Derivate des Methylendioxybenzols. 35. Eine neue Synthese der Verbindungen 3.6-Dihydroxy-2-äthylbenzochinon-(1.4), Embelin, Vilangin, Rapanon, Dihydromaesachinon, Bhogatin, Spinulosin und Oosporein [Derivatives of methylenedioxybenzene. 35. A novel synthesis of 3,6 dihydroxy-2-ethyl-1,4-benzoquinone, embelin, vilangin, rapanone, dihydromaesaquinone, bhogatin, spinulosin and oosporein]. Chem Ber. 1972;105(2):614-24. German. doi: 10.1002/cber.19721050227. PMID: 4645596. 15: Shah V, Sunder R, de Souza NJ. Chonemorphine and rapanone--antiparasitic agents from plant sources. J Nat Prod. 1987 Jul-Aug;50(4):730-1. doi: 10.1021/np50052a026. PMID: 3430168. 16: Huo D, Sun L, Zhang L, Ru X, Liu S, Yang H. Metabolome responses of the sea cucumber Apostichopus japonicus to multiple environmental stresses: Heat and hypoxia. Mar Pollut Bull. 2019 Jan;138:407-420. doi: 10.1016/j.marpolbul.2018.11.063. Epub 2018 Dec 5. PMID: 30660290. 17: Cordero CP, Gómez-González S, León-Acosta CJ, Morantes-Medina SJ, Aristizabal FA. Cytotoxic activity of five compounds isolated from Colombian plants. Fitoterapia. 2004 Mar;75(2):225-7. doi: 10.1016/j.fitote.2003.12.017. PMID: 15030931. 18: Schulz KH, Garbe I, Hausen BM, Simatupang MH. The sensitizing capacity of naturally occurring quinones. Experimental studies in guinea pigs. II. Benzoquinones. Arch Dermatol Res. 1979 May 4;264(3):275-86. doi: 10.1007/BF00412654. PMID: 464645. 19: Lund AK, Adsersen A, Nyman U. Biological activities of benzoquinones from Badula barthesia and Embelia angustifolia. Phytomedicine. 1998 May;5(3):199-203. doi: 10.1016/S0944-7113(98)80028-7. PMID: 23195841. 20: Omosa LK, Midiwo JO, Mbaveng AT, Tankeo SB, Seukep JA, Voukeng IK, Dzotam JK, Isemeki J, Derese S, Omolle RA, Efferth T, Kuete V. Antibacterial activities and structure-activity relationships of a panel of 48 compounds from Kenyan plants against multidrug resistant phenotypes. Springerplus. 2016 Jun 27;5(1):901. doi: 10.1186/s40064-016-2599-1. PMID: 27386347; PMCID: PMC4923020.