5-Heptadecylresorcinol (AR-C17) is a phenolic lipid component and an orally bioavailable mitochondrial protectant. 5-Heptadecylresorcinol improves mitochondrial function through the sirtuin3 signaling pathway, thereby reducing endothelial cell damage and apoptosis. 5-Heptadecylresorcinol induces sirtuin3-mediated autophagy. 5-Heptadecylresorcinol reduces atherosclerotic plaque in the aortic root zone of mouse hearts. 5-Heptadecylresorcinol may be utilized in studies to prevent atherosclerosis and obesity.

Physicochemical Properties

Molecular Formula	C23H40O2
Exact Mass	348.302
CAS #	41442-57-3
PubChem CID	181700
Appearance	Off-white to light yellow solid powder
Density	1.0±0.1 g/cm3
Boiling Point	478.0±15.0 °C at 760 mmHg
Melting Point	91 - 93 °C
Flash Point	202.6±15.0 °C
Vapour Pressure	0.0±1.2 mmHg at 25°C
Index of Refraction	1.507
LogP	9.72
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	16
Heavy Atom Count	25
Complexity	269
Defined Atom Stereocenter Count	0
InChi Key	BBGNINPPDHJETF-UHFFFAOYSA-N
InChi Code	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
Chemical Name	5-heptadecylbenzene-1,3-diol
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	SIRT3
ln Vitro	5-Heptadecylresorcinol boosts SIRT3 in HUVECs [1] to reduce mitochondrial dysfunction at 0, 0.5, 1, and 2 µM during a 24-hour period. 5-Heptadecylresorcinol reduces mitochondrial damage and adipocyte lipolysis brought on by inflammatory conditioned medium (CM), while also reducing the generation of reactive oxygen species inside the mitochondria and the depolarization of the mitochondrial membrane [2]. By decreasing the release of glycerol from 3T3-L1 adipocytes, 5-Heptadecylresorcinol (5, 10 and 15 μM; 24 hours) significantly inhibits CM-induced lipolysis in adipocytes [2]. 5-Adipocytes with CM-induced mitochondrial dysfunction are improved by 5-Heptadecylresorcinol (5, 10 and 15 μM; 24 hours) [2].
ln Vivo	5-Heptadecylresorcinol (30 mg/kg, 150 mg/kg; taken orally daily for 16 weeks) enhances lipid metabolism in mice fed a high-fat diet that are ApoE−/− [1]. 5-Heptadecylresorcinol improves body weight and decreases mitochondrial dysfunction and adipose tissue macrophage infiltration in mice when given orally every day for 16 weeks (30 mg/kg, 150 mg/kg) [2].
Cell Assay	Western Blot Analysis[2] Cell Types: 3T3-L1 adipocytes Tested Concentrations: 5, 10 and 15 μM Incubation Duration: 24 hrs (hours) Experimental Results: Increased the expression of UCP1, COX IV, PGC-1α, DRP1 and MFN2 proteins.
Animal Protocol	Animal/Disease Models: C57BL/6J mice[1][2] Doses: 30 mg/kg, 150 mg/kg Route of Administration: PO; daily for 16 weeks Experimental Results: Lowered serum total cholesterol, triglyceride, VLDL-C, and LDL-C levels[1]. diminished adipose tissue macrophage infiltration from high-fat diet induced obese C57BL/6J mice[2].
References	[1]. The Pharmacological Activity of Garlic (Allium sativum) in Parkinson's Disease: From Molecular Mechanisms to the Therapeutic Potential. ACS Chem Neurosci. 2023 Mar 15;14(6):1033-1044. [2]. Neuroprotective effects of Z-ajoene, an organosulfur compound derived from oil-macerated garlic, in the gerbil hippocampal CA1 region after transient forebrain ischemia. Food Chem Toxicol. 2014 Oct;72:1-7.
Additional Infomation	5-heptadecylresorcinol is a 5-alkylresorcinol that is resorcinol which is substituted by a heptadecyl group at position 5. It is found in wheat bran. It has a role as an antineoplastic agent and a plant metabolite. 5-Heptadecylbenzene-1,3-diol has been reported in Hordeum vulgare, Secale cereale, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)