20056-66-0

Basic information

• Product Name: 3-PENTYL-PHENOL
• Synonyms: 3-PENTYL-PHENOL;m-pentylphenol;Einecs 243-487-7;Phenol, 3-pentyl-
• CAS NO: 20056-66-0
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.24414
• EINECS: 243-487-7
• Mol File: 20056-66-0.mol

Chemical Properties

• Boiling Point: 265.4 °C at 760 mmHg
• Flash Point: 136.2 °C
• Appearance: /
• Density: 0.964 g/cm³
• Vapor Pressure: 0.00561mmHg at 25°C
• Refractive Index: 1.518
• PKA: 10.10±0.10(Predicted)
• CAS DataBase Reference: 3-PENTYL-PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PENTYL-PHENOL(20056-66-0)
• EPA Substance Registry System: 3-PENTYL-PHENOL(20056-66-0)

Safety Data

• Hazardous Substances Data: 20056-66-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Pentylphenol is used as an intermediate in the synthesis of (-)-Desoxycannabidiol (D296945), an analog of (-)-cannabidiol (C175300). (-)-Cannabidiol is a major non-psychoactive constituent of Cannabis, which has gained significant attention for its potential therapeutic applications. The synthesis of (-)-Desoxycannabidiol involves the use of 3-Pentylphenol as a key component, highlighting its importance in the development of novel therapeutic agents.
Used in Chemical Synthesis:
3-Pentylphenol is also used as a building block in the synthesis of various organic compounds due to its reactive phenolic hydroxyl group and the presence of a pentyl chain. This makes it a versatile starting material for the production of a wide range of chemicals, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Research and Development:
3-Pentylphenol is utilized in research and development for the study of its bioactivities and potential applications in various fields. The compound has been found to exhibit anticonvulsant, anxiolytic, and anti-inflammatory effects, making it a valuable tool for understanding the mechanisms of these conditions and the development of new treatments.

InChI:InChI=1/C11H16O/c1-2-3-4-6-10-7-5-8-11(12)9-10/h5,7-9,12H,2-4,6H2,1H3

Upstream product

• 20056-57-9 1-methoxy-3-pentylbenzene 
• 60441-55-6 1-(3'-methoxyphenyl)-pentan-1-ol 
• 126983-64-0 (E)-1-methoxy-3-(pent-1-en-1-yl)benzene 
• 109-65-9 1-bromo-butane 
• 108-39-4 3-methyl-phenol 
• 2398-37-0 3-methoxyphenyl bromide 
• 110-53-2 1-Bromopentane 
• 824-98-6 m-methoxybenzyl chloride 
• 591-31-1 3-methoxy-benzaldehyde 
• 6971-51-3 3-methoxybenzyl alcohol 
• 20359-55-1 1-(3-methoxyphenyl)pentan-1-one 
• 5813-86-5 m-methoxybenzamide 
• 1700-37-4 3-Benzyloxybenzaldehyde 
• 50673-94-4 1-(3'-benzyloxyphenyl)pentan-1-ol 

Downstream Products

• 132537-29-2 3-acetoxy-1-pentylbenzene 
• 129679-24-9 2-{1-[(E)-2-Hydroxy-propylimino]-ethyl}-5-pentyl-phenol 
• 1417520-13-8 C₁₂H₁₅ClO₂ 
• 1002101-15-6 3-pentylphenyl trifluoromethanesulfonate 
• 1415961-22-6 diethyl 2-[(1R,6R)-3-methyl-6-(1-prop-1-en-2-yl)-cyclohex-2-enyl]-5-pentylphenyl phosphate 
• 1381973-51-8 [(1R,6R)-3-methyl-6-(1-prop-1-en-2-yl)-cyclohex-2-enyl]-4-pentylbenzene 
• 133328-73-1 1-methyl-4-tosyloxymethyl-5-(2-methoxy-4-n-pentylphenyl)-cyclohex-1-ene 
• 133301-55-0 2-(2-methoxy-4-n-pentylphenyl)-4-methylcyclohexaneacetic acid 
• 133301-54-9 1-methyl-4-carboxymethyl-5-(2-methoxy-4-n-pentylphenyl)-cyclohex-1-ene 
• 133301-50-5 1-methyl-5-(2-methoxy-4-n-pentylphenyl)cyclohex-1-ene-4-carboxylic acid 
• 133301-53-8 1-methyl-4-cyanomethyl-5-(2-methoxy-4-n-pentylphenyl)-cyclohex-1-ene 
• 133301-51-6 1-methyl-4-hydroxymethyl-5-(2-methoxy-4-n-pentylphenyl)-cyclohex-1-ene 
• 133301-52-7 1-methyl-4-chloromethyl-5-(2-methoxy-4-n-pentylphenyl)-cyclohex-1-ene 
• 133301-49-2 2-methoxy-4-n-pentylcinnamic acid 

Relevant articles and documents

The design, synthesis and testing of desoxy-CBD: Further evidence for a region of steric interference at the cannabinoid receptor

Cannabidiol CBD, a non-psychoactive constituent of marihuana, has been reported to possess essentially no affinity for cannabinoid CB1 receptor binding sites in the brain. Our hypothesis concerning CBD's lack of affinity for the cannabinoid CB1 receptor is that CBD is not capable of clearing a region of steric interference at the CB1 receptor and thereby not able to bind to this receptor. We have previously characterized this region of steric interference at the CB1 receptor [P.H. Reggio, A.M. Panu, S. Miles J. Med. Chem. 36, 1761-1771 (1993)] in three dimensions using the Active Analog Approach. We report here a conformational analysis of CBD which, in turn, led to the design of a new analog, desoxy-CBD. Modeling results for desoxy-CBD predict that this compound is capable of clearing the region of steric interference by expending 3.64 kcal/mol of energy in contrast to the 12.39 kcal/mol expenditure required by CBD. Desoxy-CBD was synthesized by condensation of 3-pentylphenol with p-mentha-2,8-dien-1-ol mediated by DMF-dineopental acetal. Desoxy-CBD was found to behave as a partial agonist in the mouse vas deferens assay, an assay which is reported to detect the presence of cannabinoid receptors. The compound produced a concentration related inhibition of electrically-evoked contractions of the mouse vas deferens, possessing an IC50 of 30.9 nM in this assay. Taken together, these results support the hypothesis of the existence of a region of steric interference at the CB1 receptor. While the energy expenditure to clear this region was too high for the parent compound, CBD, the removal of the C6' hydroxyl of CBD produced a molecule (desoxy-CBD) able to clear this region and produce activity, albeit at a reduced level.

COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF THERAPEUTIC AGENTS

The disclosure features novel lipids and compositions involving the same. Nanoparticle compositions include a novel lipid as well as additional lipids such as phospholipids, structural lipids, and PEG lipids. Nanoparticle compositions further including therapeutic and/or prophylactics such as RNA are useful in the delivery of therapeutic and/or prophylactics to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.

COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF THERAPEUTIC AGENTS

The disclosure features novel lipids and compositions involving the same. Nanoparticle compositions include a novel lipid as well as additional lipids such as phospholipids, structural lipids, and PEG lipids. Nanoparticle compositions further including therapeutic and/or prophylactics such as RNA are useful in the delivery of therapeutic and/or prophylactics to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.

Improved accessibility to the desoxy analogues of Δ9- tetrahydrocannabinol and cannabidiol

Desoxy analogues of Δ9-tetrahydrocannabinol (THC) and cannabidiol (CBD) have been reported to provide a novel mode of analgesia whilst avoiding the psychotropic side effects associated with most cannabinoid drugs. A detailed and improved synthesis of desoxy THC, desoxy CBD and didesoxy CBD is reported here. The key improvements include a concentration-dependent boron trifluoride mediated electrophilic aromatic substitution which was used to synthesize both THC and CBD analogues. The synthetic route is general and could be applied to the development of a library of modified desoxy THC and desoxy CBD analogues.

A 'meta effect' in the fragmentation reactions of ionised alkyl phenols and alkyl anisoles

The competition between benzylic cleavage (simple bond fission [SBF]) and retro-ene rearrangement (RER) from ionised ortho, meta and para RC 6H4OH and RC6H4OCH3 (R = n-C3H7, n-C4H9, n-C5H11, n-C7H15, n-C9H19, n-C 15H31) is examined. It is observed that the SBF/RER ratio is significantly influenced by the position of the substituent on the aromatic ring. As a rule, phenols and anisoles substituted by an alkyl group in meta position lead to more abundant methylene-2,4-cyclohexadiene cations (RER fragmentation) than their ortho and para homologues. This 'meta effect' is explained on the basis of energetic and kinetic of the two reaction channels. Quantum chemistry computations have been used to provide estimate of the thermochemistry associated with these two fragmentation routes. G3B3 calculation shows that a hydroxy or a methoxy group in the meta position destabilises the SBF and stabilises the RER product ions. Modelling of the SBF/RER intensities ratio has been performed assuming two single reaction rates for both fragmentation processes and computing them within the statistical RRKM formalism in the case of ortho, meta and para butyl phenols. It is clearly demonstrated that, combining thermochemistry and kinetics, the inequality (SBF/RER) metaorthopara holds for the butyl phenols series. It is expected that the 'meta effect' described in this study enables unequivocal identification of meta isomers from ortho and para isomers not only of alkyl phenols and alkyl anisoles but also in other alkyl benzene series. Copyright

Scope and limitations of lithium-ethylenediamine-THF-mediated cleavage at the α-position of aromatics: Deprotection of aryl methyl ethers and benzyl ethers under mild conditions

The scope and limitation of lithium-ethylenediamine-THF-mediated reductive bond cleavage at the α-position of aromatics were examined. Very mild conditions such as lithium metal (5 equiv) and ethylenediamine (7 equiv) in oxygen-free THF were quite effective for the demethylation of aromatic ethers even at as low as -10°C. Allyl benzyl ethers were also deprotected under these conditions with very little change of the allylic alcohol moiety. Through this study, 2,6-dimethylbenzyl (m-xylylmethyl, MXM) group was developed as an alternative of benzyl group, which is readily cleavable under the above mentioned reductive conditions.

Interaction of alkoxides. XVIII. Utilitization of the complex base from alkyllithium and potassium alkoxides in the dimetallation of phenol, thiophenol, o-, m- and p-cresol

Successful O- and ortho-ring metallation of phenol and side chain metallation in o-cresol has been achieved by use of a mixture of two molar equivalents of n-butyllithium, one molar equivalent of potassium t-butoxide and two molar equivalents of N,N,N',N'-tetramethylethylene diamine in hexane.Poor results were obtained with m-cresol, thiophenol and p-cresol. m-Cresol was effectively dimetallated with a mixture of two molar equivalents of tBuOK and two molar equivalents of nBuLi*TMEDA.The effectiveness of another type of complex base based on 2-ethylhexyllithium (EhexLi) and potassium alkoxides has been also investigated, especially in respect of the influence of the concentration and the ctructure of the alkoxide used.With a complex base from EhexLi and 3 equivalents of potassium 3-methyl-3-pentoxide phenol was successfuly dimetallated even in the absence of TMEDA.Thus, the enhanced reactivity of a complex base containing a higher concentration of a more branched potassium alkoxide over that of previously used complex bases has been confirmed.

REDUCTIVE TRANSFORMATIONS WITH TRIMETHYLSILYL CHLORIDE-SODIUM IODIDE. A NEW SYNTHESIS OF 4H-1,3-OXAZINES

1-Arylalkenes and 1-arylalkanols are reduced to arylalkanes on heating with trimethylsilyl chloride/sodium iodide in CH3CN.Under similar conditions enones, dialkylated in the β-position of the double bond, give 4H-1,3-oxazines.

Naturally Occurring Dibenzofurans. VIII The Synthesis of Isodidymic acid

The synthesis of the lichen dibenzofuran isodidymic acid (2) (3-hydroxy-7-methoxy-9-pentyl-1-propyldibenzofuran-2-carboxylic acid) by intramolecular Ullmann coupling of methyl 3-iodo-4-(2'-iodo-5'-methoxy-3'-pentylphenoxy)-6-methoxy-2-propylbenzoate (22), and further transformations, is described.