Embelin

Embelin
Names
	Preferred IUPAC name 2,5-Dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
	Other names Embelic acid, Emberine
Identifiers
CAS Number	550-24-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:4778;
ChEMBL	ChEMBL221137;
ChemSpider	3105;
ECHA InfoCard	100.008.164
EC Number	208-979-8;
KEGG	C10342;
PubChem CID	3218;
UNII	SHC6U8F5ER ;
CompTox Dashboard (EPA)	DTXSID80203537 ;
	InChI InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3 Key: IRSFLDGTOHBADP-UHFFFAOYSA-N;
	SMILES CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O;
Properties
Chemical formula	C17H26O4
Molar mass	294.391 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H361
Precautionary statements	P201, P202, P281, P308+P313, P405, P501
Related compounds
Related compounds	Rapanone
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Embelin, also known as 2,5-dihydroxy-3-undecyl-1,4-benzoquinone, is a naturally occurring para-benzoquinone isolated from dried berries of Embelia ribes plants.^[1]^[2] Several studies have reported antidiabetic activity of embelin.^[3] Embelin is known to act as a highly potent and selective GPR84 agonist.^[4]^[5] It has been found to produce pro-inflammatory effects and cognitive impairment in rodents.^[6]

References

↑ Radhakrishnan, N., & Gnanamani, A. (2014). 2, 5-dihydroxy-3-undecyl-1, 4-benzoquinone (Embelin)-A second solid gold of India-A Review. International Journal Pharmacy & Pharmaceutical Sciences, 6(6), 23-30.
↑ Poojari, R. (2014). Embelin–a drug of antiquity: shifting the paradigm towards modern medicine. Expert opinion on investigational drugs, 23(3), 427-444. PMID 24397264 doi:10.1517/13543784.2014.867016
↑ Durg, S., Veerapur, V. P., Neelima, S., & Dhadde, S. B. (2017). Antidiabetic activity of Embelia ribes, embelin and its derivatives: A systematic review and meta-analysis. Biomedicine & Pharmacotherapy, 86, 195-204. PMID 27984799 doi:10.1016/j.biopha.2016.12.001
↑ Wei L, Tokizane K, Konishi H, Yu HR, Kiyama H (October 2017). "Agonists for G-protein-coupled receptor 84 (GPR84) alter cellular morphology and motility but do not induce pro-inflammatory responses in microglia". J Neuroinflammation. 14 (1) 198. doi:10.1186/s12974-017-0970-y. PMC 5627487. PMID 28974234.
↑ Gaidarov I, Anthony T, Gatlin J, Chen X, Mills D, Solomon M, Han S, Semple G, Unett DJ (May 2018). "Embelin and its derivatives unravel the signaling, proinflammatory and antiatherogenic properties of GPR84 receptor". Pharmacol Res. 131: 185–198. doi:10.1016/j.phrs.2018.02.021. PMID 29471103.
↑ Cox TO, Devason AS, de Araujo A, Mason S, Subramanian M, Salvador AF, Descamps HC, Kim J, Zhu Y, Litichevskiy L, Jung S, Song WS, Cortés-Martín A, Henderson NT, Huang KP, Nguyen T, Sae-Lee W, Umana IC, Sacta M, Rahman RJ, Wisser S, Nelson JA, Golynker I, McSween AM, Hohmann EF, Patel S, Bub AL, Soekler C, Blank N, Hoxha K, Boccia L, Wong AC, Bahnsen K, Kim J, Biderman N, Abbasian D, Shoffler C, Petucci C, McAllister FE, Alhadeff AL, Fuccillo MV, Hill C, Jang C, Betley JN, de Lartigue G, Lee VY, Levy M, Thaiss CA (April 2026). "Intestinal interoceptive dysfunction drives age-associated cognitive decline". Nature. 652 (8109): 442–450. Bibcode:2026Natur.652..442C. doi:10.1038/s41586-026-10191-6. PMC 13061634. PMID 41813891.

[1] Radhakrishnan, N., & Gnanamani, A. (2014). 2, 5-dihydroxy-3-undecyl-1, 4-benzoquinone (Embelin)-A second solid gold of India-A Review. International Journal Pharmacy & Pharmaceutical Sciences, 6(6), 23-30.

[2] Poojari, R. (2014). Embelin–a drug of antiquity: shifting the paradigm towards modern medicine. Expert opinion on investigational drugs, 23(3), 427-444. PMID 24397264 doi:10.1517/13543784.2014.867016

[3] Durg, S., Veerapur, V. P., Neelima, S., & Dhadde, S. B. (2017). Antidiabetic activity of Embelia ribes, embelin and its derivatives: A systematic review and meta-analysis. Biomedicine & Pharmacotherapy, 86, 195-204. PMID 27984799 doi:10.1016/j.biopha.2016.12.001

[WeiTokizaneKonishi2017-4] Wei L, Tokizane K, Konishi H, Yu HR, Kiyama H (October 2017). "Agonists for G-protein-coupled receptor 84 (GPR84) alter cellular morphology and motility but do not induce pro-inflammatory responses in microglia". J Neuroinflammation. 14 (1) 198. doi:10.1186/s12974-017-0970-y. PMC 5627487. PMID 28974234.

[GaidarovAnthonyGatlin2018-5] Gaidarov I, Anthony T, Gatlin J, Chen X, Mills D, Solomon M, Han S, Semple G, Unett DJ (May 2018). "Embelin and its derivatives unravel the signaling, proinflammatory and antiatherogenic properties of GPR84 receptor". Pharmacol Res. 131: 185–198. doi:10.1016/j.phrs.2018.02.021. PMID 29471103.

[CoxDevasondeAruajo2026-6] Cox TO, Devason AS, de Araujo A, Mason S, Subramanian M, Salvador AF, Descamps HC, Kim J, Zhu Y, Litichevskiy L, Jung S, Song WS, Cortés-Martín A, Henderson NT, Huang KP, Nguyen T, Sae-Lee W, Umana IC, Sacta M, Rahman RJ, Wisser S, Nelson JA, Golynker I, McSween AM, Hohmann EF, Patel S, Bub AL, Soekler C, Blank N, Hoxha K, Boccia L, Wong AC, Bahnsen K, Kim J, Biderman N, Abbasian D, Shoffler C, Petucci C, McAllister FE, Alhadeff AL, Fuccillo MV, Hill C, Jang C, Betley JN, de Lartigue G, Lee VY, Levy M, Thaiss CA (April 2026). "Intestinal interoceptive dysfunction drives age-associated cognitive decline". Nature. 652 (8109): 442–450. Bibcode:2026Natur.652..442C. doi:10.1038/s41586-026-10191-6. PMC 13061634. PMID 41813891.

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Embelin

See also

References