500-66-3
3,5-hydroxypentylbenzene
CAS: 500-66-3
Molecular Formula: C11H16O2
500-66-3 - Names and Identifiers
| Name | 3,5-hydroxypentylbenzene |
| Synonyms | Olivetol Oilvetol OLIVETOL AURORA KA-7378 n-Amylresolcinol 5-AMYL RESORCINOL 5-Pentylresorcinol 5-PENTYLRESORCINOL 5-N-PENTYLRESORCINOL 5-pentyl-3-benzenediol 3,5-dihydro-amylbenzene 5-pentylbenzene-1,3-diol 5-PENTYL 1,3-BENZENEDIOL 3,5-hydroxypentylbenzene 3,5-dihydroxyamylbenzene 5-Pentyl-1,3-benzenediol Pentyl-3,5-dihydroxybenzene 5-Pentyl3,5-Dihydroxyamylbenzene |
| CAS | 500-66-3 |
| EINECS | 207-908-8 |
| InChI | InChI=1/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3 |
| InChIKey | IRMPFYJSHJGOPE-UHFFFAOYSA-N |
500-66-3 - Physico-chemical Properties
| Molecular Formula | C11H16O2 |
| Molar Mass | 180.24 |
| Density | 1.068±0.06 g/cm3(Predicted) |
| Melting Point | 46-48°C(lit.) |
| Boling Point | 164 °C |
| Flash Point | >230°F |
| Solubility | Soluble in water (partly miscible), chloroform, and methanol. |
| Vapor Presure | 0.000273mmHg at 25°C |
| Appearance | Solid |
| Color | Colourless to Beige Oil to Low-Melting |
| pKa | 9.59±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Stability | Light Sensitive |
| Refractive Index | 1.546 |
| MDL | MFCD00002293 |
| In vitro study | Olivetol inhibits the (S)-mephenytoin 4'-hydroxylase activity of CYP2C19 activity with an IC 50 of 15.3 μM and a K i of 2.71 μM. Olivetol also inhibits AMMC O-demethylase activity of recombinant CYP2D6 with an IC 50 of 7.21 μM and a K i of 2.87 μM. Olivetol is a competitive inhibitor of the cannabinoid receptors CB1 and CB2. |
500-66-3 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/39 - |
| WGK Germany | 3 |
| RTECS | VH2880000 |
500-66-3 - Reference Information
| update date: | 2022/11/12 10:05:38 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| background | 3,5-dihydroxyalkylbenzene has a variety of biological activities and has killing effects on fungi and bacteria of various pathogens. In recent years, it has been found that high concentrations of 3, 5-dihydroxyalkylbenzene can break DNA in the presence of copper chloride and oxygen. Therefore, it is used to inhibit and treat human immune deficiency, cancer and other malignant tumors caused by retrovirus, and the effect is remarkable. 3, 5-dihydroxyalkylbenzene can also be used to synthesize cannabinoids (cannabinoids). Cannabinoids are a general term for a class of substances with similar chemical structures related to the physiological activity of the human body in cannabis. The number exceeds 60. It can be used for pain relief, sedation, anti-inflammatory, digestive aid and anti-hypertension. The generation of this type of compound is 3,5-dihydroxypentylene (Olivetol). |
| application | 3, 5-dihydroxypentobenzene is an important pharmaceutical intermediate, which was first obtained by degrading lichen acid (also known as D-zonolic acid and pentyl lichen phenolic acid) extracted from lichen plants, and is mainly used in laboratory research and development process and chemical production process. |
| preparation | 156g of benzene, 900mL of dichloromethane and 146.5g of anhydrous aluminum trichloride are added into a 2L three-mouth flask, after the temperature is reduced to 0-5 ℃, 120.5g of n-valeryl chloride is slowly added dropwise, and the internal temperature is maintained at 0-10 ℃ during the dropping process. After dropping, the temperature is increased to 40 ℃, and the reaction is stirred for 2 hours. Under the cooling of ice bath, slowly add 500mL of 1N hydrochloric acid solution dropwise, and separate the solution after dropwise addition. The aqueous phase was extracted with 400mLDCM. After combining the organic phase, 142g of benzopentanone was obtained by concentration and vacuum distillation with 87% yield. in a 1L three-mouthed flask, control 200mL of fuming nitric acid and 200 mL5% sulfuric acid to form mixed acid within 20 ℃, then cool down to within 10 ℃, slowly add 129.6g of benvalerone dropwise, and control the internal temperature in the dropwise process to 0-10 ℃. After dropping the heat preservation reaction for 2 hours, the temperature is raised to 50 ℃, and then the reaction is carried out for 5 hours. After cooling to 20 ℃, the reaction liquid is poured into crushed ice, solid is precipitated, filtered, the filter cake is dissolved with DCM and then separated, and the organic phase is reconcentrated to obtain crude product. The crude product was dissolved and crystallized by PE and EA, dissolved and dried to obtain 156.5g of 3,5-dinitrobenzophenone with 78% yield and 98.3% purity. |
| Use | 3, 5-dihydroxypentylbenzene is a precursor for tetrahydrocannabinol-related synthesis. |
| biological activity | Olivetol is a natural polyphenolic compound that exists in lichens or is produced by some insects. Olivetol competitively inhibited the activities of cannabinoid receptors CB1 and CB2, CYP2C19 and CYP2D6, the IC50 and Ki values were 15.3 μM, 7.21 μM and 2.71 μM, 2.87 μM, respectively. |
| Target | Value |
| CB1 (Cell-free) | |
| CB2 (Cell-free) | |
| CYP1A1 (Cell-free) | 13.8 μM |
| CYP2C19 (Cell-free) | 15.3 μM |
Last Update：2024-04-09 19:05:12
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