500-49-2 Usage
Description
5-Propyl-1,3-benzenediol, also known as 5-Propylbenzene-1,3-diol, is a white to brown crystalline solid that serves as an intermediate in the preparation of various compounds. It is characterized by its unique chemical structure, which contributes to its specific properties and applications.
Uses
Used in Pharmaceutical Industry:
5-Propyl-1,3-benzenediol is used as an intermediate for the preparation of Cannabigerovarin (C175140), a compound that stimulates thermosensitive transient receptor potential (TRP) channels of vanilloid type-4 (TRPV4). This stimulation leads to an increase in intracellular calcium ion concentration ([Ca2+]i) with moderate-high efficacy (30-60% of the effect of ionomycin) and potency (EC50 0.9-6.4 μM). 5-Propyl-1,3-benzenediol has potential applications in the development of drugs targeting TRPV4 channels, which are involved in various physiological processes and diseases.
Synthesis
In a 100 mL round bottom flask, open to the atmosphere was added the crude product Benzene, 1,3-dimethoxy-5-propyl (0.736 g, 4.08 mmol, 1.0 equiv.) and a 1:1 mixture of glacial acetic acid (20 mL, 349.7 mmol, 17.4 M) and hydrobromic acid (48% in H2O, 20 mL, 368.3 mmol, 18.4 M). The reaction mixture was refluxed at 125 °C for 3 hours while stirring, or until the starting material was consumed via TLC analysis. At this point, the reaction was allowed to cool to room temperature and quenched by the addition of DI H2O. The biphasic solution was added to a separatory funnel, wherein the organic portion was extracted Et2O (ca. 3x 20 mL). The organic layers were then combined, neutralized with a concentrated sodium bicarbonate solution (ca. 30 mL), washed with a saturated brine solution (ca. 50 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford the final product without 5-Propyl-1,3-benzenediol (0.609 g, 99% yield) as a pale yellow oil.
Solubility in organics
5-Propyl-1,3-benzenediol is soluble in N,N-dimethylformamide, soluble in methanol, slightly soluble in glacial acetic acid, very slightly soluble in chloroform, almost insoluble in water.
Check Digit Verification of cas no
The CAS Registry Mumber 500-49-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 0 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 500-49:
(5*5)+(4*0)+(3*0)+(2*4)+(1*9)=42
42 % 10 = 2
So 500-49-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H12O2/c1-2-3-7-4-8(10)6-9(11)5-7/h4-6,10-11H,2-3H2,1H3
500-49-2Relevant articles and documents
Cannabidiol derivative as well as preparation method and medical application thereof
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Paragraph 0153; 0156; 0163-0168, (2021/07/10)
The invention relates to a cannabidiol derivative and application thereof in medicine, in particular to a pyrimidine derivative as shown in a general formula (I), or a stereoisomer, a solvate, a metabolite, a prodrug, a pharmaceutically acceptable salt or a co-crystal thereof, and definition of each substituent in the general formula (I) is the same as that in the specification.
Using (+)-carvone to access novel derivatives of (+)-ent-cannabidiol: The first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV
Golliher, Alexandra E.,Tenorio, Antonio J.,Dimauro, Nina O.,Mairata, Nicolas R.,Holguin, F. Omar,Maio, William
, (2021/02/20)
(?)-Cannabidiol [(?)-CBD] has recently gained prominence as a treatment for neuro-inflammation and other neurodegenerative disorders; interest is also developing in its synthetic enantiomer, (+)-CBD, which has a higher affinity to CB1/CB2 receptors than the natural stereoisomer. We have developed an inexpensive, stereoselective route to access ent-CBD derivatives using (+)-carvone as a starting material. In addition to (+)-CBD, we report the first syntheses of (+)-cannabidivarin, (+)-cannabidiphorol as well as C-6/C-8 homologues.
BIOENZYMATIC SYNTHESIS OF THC-v, CBV AND CBN AND THEIR USE AS THERAPEUTIC AGENTS
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Paragraph 0145; 0146, (2017/10/18)
The present invention provides methods for producing cannabinoids. More specifically, the invention is directed to the bio-enzymatic synthesis of THC-v, CBV and CBN by contacting a compound according to Formula I with a cannabinoid synthase enzyme. Also described is a system for producing these pharmaceutically important cannabinoids and the use of such cannabinoids as therapeutic agents.