Physicochemical Properties
| Molecular Formula | C31H64 |
| Molecular Weight | 436.84 |
| Exact Mass | 436.501 |
| CAS # | 630-04-6 |
| PubChem CID | 12410 |
| Appearance | White to off-white solid powder |
| Density | 0.808g/cm3 |
| Boiling Point | 180 °C / 4mmHg |
| Melting Point | 67-69 °C |
| Flash Point | 313.1ºC |
| Index of Refraction | 1.451 |
| LogP | 12.339 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 28 |
| Heavy Atom Count | 31 |
| Complexity | 254 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C([H])([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] |
| InChi Key | IUJAMGNYPWYUPM-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C31H64/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-31H2,1-2H3 |
| Chemical Name | hentriacontane |
| 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
| ln Vitro | Hentriacontane (1, 5, 10 μM, 1h) can reduce inflammatory parameters such as TNF-a, IL-6 and IL-1b in RAW 264.7 cells[1]. Hentriacontane |
| ln Vivo | Hentriacontane (1, 2, 5 mg/kg, oral, single dose) can effectively inhibit inflammatory factors in the LPS-induced mouse inflammation model[1]. |
| Cell Assay |
Western Blot Analysis[1] Cell Types: RAW 264.7 Tested Concentrations: 1, 5, 10 μM Incubation Duration: 1 h Experimental Results: Increased the phosphorylation of NF-kB p65. |
| Animal Protocol |
Animal/Disease Models: LPS-induced mice inflammation model[1] Doses: 1, 2, 5 mg/kg Route of Administration: p.o. Experimental Results: Inhibited TNFa、IL-6 and IL-1b. |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion Liver, heart, kidneys, muscle and adipose (perirenal and s.c.) /bovine/ tissues were collected from 6 animals for analysis of their hydrocarbon composition. Qualitative and quantitative determinations were carried out by gas chromatography and combined gas chromatography-mass spectrometry. Although differing in the proportions, a homologous series of n-alkanes ranging from n-C12-n-C31 was found in all samples. The isoprenoid hydrocarbons phytane and phytene (phyt-1-ene and phyt-2-ene) were also identified. (These findings have relevance to the health of humans consuming hydrocarbon-contaminated meats.) /n-Alkanes/ This report deals with a new human disorder characterized by the accumulation of plant long-chain n-alkanes in viscera of a human patient. Lipid analysis of tissues from an adult male after sudden death (affected with diffuse visceral granuloma containing lipophilic crystallized material) showed the presence of abnormal compounds identified as long-chain n-alkanes with 29 (n-nonacosane), 31 (n-hentriacontane) and 33 carbons (n-tritriacontane). Study of n-alkane distribution in patient tissues showed a major accumulation in lumbo-aortic lymph nodes, adrenal glands, lung (the highest levels were found in lung granulomas) and liver; significantly lower amounts were detected in myocardium and kidney, whereas no detectable level was found in brain. On the basis of the structural composition and of the tissue distribution of the accumulated n-alkanes, their dietary (plant) origin and the pathophysiological mechanism of the storage are discussed. |
| Toxicity/Toxicokinetics |
Toxicity Summary IDENTIFICATION AND USE: Hentriacontane is a higher n-alkane containing 31 carbon atoms (C31). It is used as traditional medicine and experimental therapy. HUMAN EXPOSURE AND TOXICITY: A case report described human disorder characterized by the accumulation of plant long-chain n-alkanes in viscera of a human patient. Diffuse visceral granuloma containing lipophilic crystallized material showed the presence of long-chain n-alkanes including hentriacontane. Study of n-alkane distribution in patient tissues showed a major accumulation in lumbo-aortic lymph nodes, adrenal glands, lung and liver; significantly lower amounts were detected in myocardium and kidney, whereas no detectable level was found in brain. ANIMAL STUDIES: Hentriacontane can contribute to the "paraffin liver" in cows. The very large quantities of the abnormal substance in the cow livers indicate low toxicity, and evidently accumulation over long periods of time. |
| References |
[1].Khajuria V, Gupta S, Sharma N, Kumar A, Lone NA, Khullar M, Dutt P, Sharma PR, Bhagat A, Ahmed Z. Anti-inflammatory potential of hentriacontane in LPS stimulated RAW 264.7 cells and mice model. Biomed Pharmacother. 2017 Aug;92:175-186. doi: 10.1016/j.biopha.2017.05.063. Epub 2017 May 23. PMID: 28549290. |
| Additional Infomation |
Hentriacontane is a long-chain alkane. It has a role as an antitubercular agent. Hentriacontane has been reported in Euphorbia piscatoria, Vanilla madagascariensis, and other organisms with data available. Therapeutic Uses /EXPL THER/ Oldenlandia diffusa (OD) has been used as a natural drug for the treatment of cancer in Asia and specifically in Korea. However, the antiinflammatory mechanisms employed by OD have yet to be completely understood. This study attempted to determine the effects of OD and hentriacontane, one of the constituent compounds of OD, on lipopolysaccharide (LPS)-induced inflammatory responses in mouse peritoneal macrophages. The findings of this study showed that OD inhibited the production of tumor necrosis factor (TNF)-a, interleukin (IL)-6 and prostaglandin E(2) (PGE(2)). The OD inhibited the enhanced levels of cyclooxygenase (COX)-2 and inducible nitric oxide synthase (iNOS) induced by LPS. It was shown that the antiinflammatory effect of OD occurs via the regulation of the activation of nuclear factor (NF)-kappaB and caspase-1. Moreover, hentriacontane was shown to ameliorate the expression of inflammatory mediators (TNF-a, IL-6, PGE(2), COX-2 and iNOS) and the activation of NF-kappaB and caspase-1 in LPS-stimulated peritoneal macrophages. These results provide novel insights into the pharmacological actions of OD as a potential candidate for the development of new drugs for the treatment of inflammatory diseases. /EXPL THER/ Ulcerative colitis (UC) is an inflammatory bowel disease, which is a chronic gastrointestinal disorder. Oldenlandia diffusa (OD) has been used as a traditional oriental medicine for inflammation. However, the regulatory effect and molecular mechanism of OD in intestinal inflammation are not yet understood. This study investigated the protective effect of OD in dextran sulfate sodium (DSS)-induced colitis. Mice treated with DSS showed remarkable clinical signs, including weight loss, and reduced colon length. Administration of OD attenuated these signs and significantly suppressed levels of interleukin (IL)-6, IL-1beta and expression of cyclooxygenase-2 in DSS-treated colon tissues. OD also reduced the activation of transcription nuclear factor-kappaB p65 in DSS-treated colon tissues. Hentriacontane, a constituent of OD, attenuated weight loss, colon shortening, and levels of IL-6 caused by DSS. Taken together, the results provide experimental evidence that OD might be a useful therapeutic medicine for patients with UC. /EXPL THER/ One of the therapeutic approaches in treating diabetes is to reduce postprandial hyperglycemia by inhibiting major carbohydrate hydrolyzing enzymes. In the present study, crude extracts of marine seaweed, Turbinaria ornata, were tested for their antidiabetic potential using enzyme inhibitory assays (a-amylase, a-glucosidase, and dipeptidyl peptidase-IV). Among the tested extracts, methanol and acetone extracts showed significant inhibitory effects on a-amylase (IC50 250.9 ug/mL), a-glucosidase (535.6 ug/mL), and dipeptidyl peptidase-4 (55.2 ug/mL), respectively. Free radical scavenging activity of these extracts was analyzed using DPPH assay (65%). Extracts were tested for in vitro toxicity using DNA fragmentation assay, hemolytic assay, and MTT assay. None of the extracts showed toxicity in tested models. Furthermore, GC-MS analysis of lead extracts showed the presence of major compounds, hentriacontane, z, z-6, 28-heptatriactontadien-2-one, 8-heptadecene, and 1-heptacosanol. Our findings suggest that Turbinaria ornata can be used as a potential source for further in vivo studies in controlling hyperglycemia. A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis. |
Solubility Data
| Solubility (In Vitro) | Typically soluble in DMSO (e.g. 10 mM) |
| 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.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2892 mL | 11.4458 mL | 22.8917 mL | |
| 5 mM | 0.4578 mL | 2.2892 mL | 4.5783 mL | |
| 10 mM | 0.2289 mL | 1.1446 mL | 2.2892 mL |