5-Heptadecylresorcinol

5-Heptadecylresorcinol
Clinical data
Drug classSirtuin-3 (SIRT3) activator
Identifiers
  • 5-heptadecylbenzene-1,3-diol
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.190.309
Chemical and physical data
FormulaC23H40O2
Molar mass348.571 g·mol−1
3D model (JSmol)
  • CCCCCCCCCCCCCCCCCC1=CC(=CC(=C1)O)O
  • InChI=1S/C23H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21-18-22(24)20-23(25)19-21/h18-20,24-25H,2-17H2,1H3
  • Key:BBGNINPPDHJETF-UHFFFAOYSA-N

5-Heptadecylresorcinol (AR-C17) is a natural product which is found in whole grain wheat and rye along with related alkylresorcinols,[1] but since it is a component of the bran it is not found in processed products such as white flour and white bread. It acts as an activator of the enzyme SIRT3,[2][3] and has been linked to various health benefits, acting as an antiinflammatory and reducing symptoms of various aging-related conditions in animal studies such as cognitive impairment,[4] atherosclerosis[5][6] obesity,[7][8][9] and non-alcoholic fatty liver disease.[10][11]

References

  1. ^ Righetti L, Rubert J, Galaverna G, Hurkova K, Dall'Asta C, Hajslova J, et al. (February 2018). "A novel approach based on untargeted lipidomics reveals differences in the lipid pattern among durum and common wheat". Food Chemistry. 240: 775–783. doi:10.1016/j.foodchem.2017.08.020. PMID 28946342.
  2. ^ Liu J, Wang Y, Hao Y, Wang Z, Yang Z, Wang Z, et al. (March 2020). "5-Heptadecylresorcinol attenuates oxidative damage and mitochondria-mediated apoptosis through activation of the SIRT3/FOXO3a signaling pathway in neurocytes". Food & Function. 11 (3): 2535–2542. doi:10.1039/c9fo03028j. PMID 32141452.
  3. ^ Hao Y, Yang Z, Liu J, Wang Z, Speakman JR, Niu C, et al. (May 2022). "Protective effects of 5-heptadecylresorcinol against adipocyte mitochondrial dysfunction through upregulation of Sirt3-mediated autophagy". The Journal of Nutritional Biochemistry. 103 108956. doi:10.1016/j.jnutbio.2022.108956. PMID 35143951.
  4. ^ Liu J, Wang Y, Wang Z, Hao Y, Bai W, Wang Z, et al. (June 2020). "5-Heptadecylresorcinol, a Biomarker for Whole Grain Rye Consumption, Ameliorates Cognitive Impairments and Neuroinflammation in APP/PS1 Transgenic Mice". Molecular Nutrition & Food Research. 64 (11) 1901218. doi:10.1002/mnfr.201901218. PMID 32385942.
  5. ^ Hao Y, Yang Z, Li Q, Wang Z, Liu J, Wang J (May 2022). "5-Heptadecylresorcinol Protects against Atherosclerosis in Apolipoprotein E-Deficient Mice by Modulating SIRT3 Signaling: The Possible Beneficial Effects of Whole Grain Consumption". Molecular Nutrition & Food Research. 66 (9) 2101114. doi:10.1002/mnfr.202101114. PMID 35297565.
  6. ^ Zhang K, Jiang L, Xue L, Wang Y, Sun Y, Fan M, et al. (October 2023). "The Enhancement of Acylcarnitine Metabolism by 5-Heptadecylresorcinol in Brown Adipose Tissue Contributes to Improving Glucose and Lipid Levels in Aging Male Mice". Nutrients. 15 (21): 4597. doi:10.3390/nu15214597. PMC 10649465. PMID 37960251.
  7. ^ Zhang K, Li T, Li Q, Nie C, Sun Y, Xue L, et al. (January 2023). "5-Heptadecylresorcinol Regulates the Metabolism of Thermogenic Fat and Improves the Thermogenic Capacity of Aging Mice via a Sirtuin 3-Adenosine Monophosphate-Activated Protein Kinase Pathway". Journal of Agricultural and Food Chemistry. 71 (1): 557–568. Bibcode:2023JAFC...71..557Z. doi:10.1021/acs.jafc.2c07073. PMID 36535764.
  8. ^ Yang Z, Yang S, Wang Z, Hao Y, Wang Z, Wei Y, et al. (June 2023). "5-Heptadecylresorcinol alleviated high-fat diet induced obesity and insulin resistance by activating brown adipose tissue". Food & Function. 14 (11): 5001–5011. doi:10.1039/d3fo00071k. PMID 37199511.
  9. ^ Wang Z, Li Q, Yang H, Zhang D, Zhang Y, Wang J, et al. (November 2023). "5-Heptadecylresorcinol Ameliorates Obesity-Associated Skeletal Muscle Mitochondrial Dysfunction through SIRT3-Mediated Mitophagy". Journal of Agricultural and Food Chemistry. 71 (43): 16032–16042. Bibcode:2023JAFC...7116032W. doi:10.1021/acs.jafc.3c01452. PMID 37862266.
  10. ^ Zhang K, Jiang L, Xue L, Wang Y, Sun Y, Fan M, et al. (March 2024). "5-Heptadecylresorcinol Improves Aging-Associated Hepatic Fatty Acid Oxidation Dysfunction via Regulating Adipose Sirtuin 3". Nutrients. 16 (7): 978. doi:10.3390/nu16070978. PMC 11013747. PMID 38613012.
  11. ^ Yang Z, Hao Y, Wang Z, Wang Z, Ye G, Gao F, et al. (November 2025). "5-Heptadecylresorcinol ameliorates high-fat diet induced non-alcoholic fatty liver disease through modulating bile acid profile and suppressing inflammation". Journal of the Science of Food and Agriculture. 105 (14): 7944–7954. doi:10.1002/jsfa.70060. PMID 40662452.
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