Rapanone

Modify Date: 2025-08-25 18:58:24

Rapanone structure	Common Name	Rapanone
	CAS Number	573-40-0	Molecular Weight	322.43900
	Density	1.099g/cm3	Boiling Point	457ºC at 760mmHg
	Molecular Formula	C₁₉H₃₀O₄	Melting Point	142-145ºC
	MSDS	N/A	Flash Point	244.3ºC

Use of Rapanone

Rapanone is a natural benzoquinone. Rapanone exhibits a broad spectrum of biological actions, including anti-tumor, antioxidant, anti-inflammatory, antibacterial and antiparasitic. Rapanone also is a potent and selective human synovial PLA2 inhibitor, with an IC50 of 2.6 μM[1][2][3][4].

Name	2,5-dihydroxy-3-tridecylcyclohexa-2,5-diene-1,4-dione
Synonym	More Synonyms

Description	Rapanone is a natural benzoquinone. Rapanone exhibits a broad spectrum of biological actions, including anti-tumor, antioxidant, anti-inflammatory, antibacterial and antiparasitic. Rapanone also is a potent and selective human synovial PLA2 inhibitor, with an IC50 of 2.6 μM[1][2][3][4].
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Infection Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase Research Areas >> Inflammation/Immunology Signaling Pathways >> Anti-infection >> Bacterial
Target	PLA2:2.6 μM (IC50)
In Vitro	Rapanone (10-40 μM; 24 h) inhibits the cell viability, with IC50s of 35.58 μM and 27.89 μM for primary rats hepatocytes and HepG2 cells, respectively[1]. Rapanone (10-40 μM; 24 h) induces a concentration-dependent mitochondrial membrane potential dissipation, ATP depletion, hydrogen peroxide generation and, phosphatidyl serine externalization in HepG2 cells[1]. Rapanone inhibits electron transport at Complex III and promotes mitochondrial dysfunction[1].
In Vivo	Rapanone (2.5-10 mg/kg; i.p.) exhibits anti-inflammatory effects in the carrageenan paw oedema model in mice[4].
References	[1]. Andreu GLP, et, al. Rapanone, a naturally occurring benzoquinone, inhibits mitochondrial respiration and induces HepG2 cell death. Toxicol In Vitro. 2020 Mar;63:104737. [2]. Morais LS, et, al. Antileishmanial compounds from Connarus suberosus: Metabolomics, isolation and mechanism of action. PLoS One. 2020 Nov 6;15(11):e0241855. [3]. Vega-Hernández K, et, al. 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. [4]. Ospina LF, et, al. Inhibition of acute and chronic inflammatory responses by the hydroxybenzoquinonic derivative rapanone. Planta Med. 2001 Dec;67(9):791-5.

Density	1.099g/cm3
Boiling Point	457ºC at 760mmHg
Melting Point	142-145ºC
Molecular Formula	C₁₉H₃₀O₄
Molecular Weight	322.43900
Flash Point	244.3ºC
Exact Mass	322.21400
PSA	74.60000
LogP	5.09330
Index of Refraction	1.53
InChIKey	AMKNOBHCKRZHIO-UHFFFAOYSA-N
SMILES	CCCCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O

HS Code	2914690090

2-HYDROXY-5-MET...

CAS#:19833-82-0

~89%

Rapanone

CAS#:573-40-0

Literature: McErlean, Christopher S. P.; Moody, Christopher J. Journal of Organic Chemistry, 2007 , vol. 72, # 26 p. 10298 - 10301

tetradecanoyl t...

CAS#:3530-28-7

Rapanone

CAS#:573-40-0

Literature: Fieser; Chamberlin Journal of the American Chemical Society, 1948 , vol. 70, p. 74

1,3-dimethoxy-5...

CAS#:5259-04-1

Rapanone

CAS#:573-40-0

Literature: Croft,J.A. et al. Australian Journal of Chemistry, 1976 , vol. 29, p. 1979 - 1987

2-methoxy-6-tri...

CAS#:5259-06-3

Rapanone

CAS#:573-40-0

Literature: Croft,J.A. et al. Australian Journal of Chemistry, 1976 , vol. 29, p. 1979 - 1987

acetic acid,5-m...

CAS#:61621-69-0

Rapanone

CAS#:573-40-0

Literature: Croft,J.A. et al. Australian Journal of Chemistry, 1976 , vol. 29, p. 1979 - 1987

Di-O-acetyl-rap...

CAS#:2552-83-2

Rapanone

CAS#:573-40-0

Literature: Maruyama,K. et al. Journal of Organic Chemistry, 1978 , vol. 43, # 25 p. 4895 - 4898

(4-acetyloxy-3,...

CAS#:16523-32-3

Rapanone

CAS#:573-40-0

Literature: Maruyama,K. et al. Journal of Organic Chemistry, 1978 , vol. 43, # 25 p. 4895 - 4898

2,5-bis-methyla...

CAS#:21772-30-5

Rapanone

CAS#:573-40-0

Literature: Asano; Yamaguchi Yakugaku Zasshi, 1940 , vol. 60, p. 585,587, 591; engl. Ref. S. 237, 239, 242 Chem.Abstr., 1942 , p. 81

Precursor 7
CAS#:19833-82-0 2-HYDROXY-5-MET... CAS#:3530-28-7 tetradecanoyl t... CAS#:5259-04-1 1,3-dimethoxy-5... CAS#:5259-06-3 2-methoxy-6-tri...
CAS#:61621-69-0 acetic acid,5-m... CAS#:2552-83-2 Di-O-acetyl-rap... CAS#:16523-32-3 (4-acetyloxy-3,...
DownStream 4
CAS#:2570-24-3 2-oxohexadecano... CAS#:544-63-8 Myristic acid CAS#:13917-35-6 ARDISIN CAS#:19833-82-0 2-HYDROXY-5-MET...

HS Code	2914690090
Summary	2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Rapanone

2,4-DIHYDRO-4-PHENYL-3H-1,2,4-TRIAZOL-3-ONE

2,5-dihydroxy-3-tridecyl-1,4-benzoquinone

2,5-Dihydroxy-3-tridecyl-benzo<1,4>chinon

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Shanghai Nianxing Industrial Co., Ltd
China
Product Name: RAPANONE
Price: Check
Purity: 99.0%
Delivery: 10 Day
Contact: Yang
Email: sales@echemcloud.com

DC Chemicals Limited
China
Product Name: Rapanone
Price: ￥Inquiry/1g
Purity: 98.9%
Delivery: 1 Day
Contact: Tony Cao
Email: sales@dcchemicals.com

Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: 2,5-Cyclohexadiene-1,4-dione,2,5-dihydroxy-3-tridecyl-
Price: $Inquiry/100g $Inquiry/1kg $Inquiry/100kg $Inquiry/1000kg
Purity: 98.0%
Delivery: Inquiry
Contact: Ms Wang
Email: enquiry@dycnchem.com

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The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.