1242-67-7 Usage
Uses
Lipoxygenases (LOs) are non-heme iron-containing dioxygenases that catalyze the oxidation of polyunsaturated fatty acids to generate unsaturated fatty acid hydroperoxides. The immediate products of 15-LO fatty acid oxidation act as mediators in inflammation, thrombosis, and cancer. CBDD is a cannabidiol derivative that potently and selectively inhibits 15-LO with an IC50 value of 0.28 μM. It does not inhibit 5-LO effectively (IC50 >200 μM).
Biological Activity
cannabidiol dimethyl ether (cbdd) is a cannabidiol derivative that potently and selectively inhibits 15-lox with an ic50 value of 0.28 μm.15-lox can oxygenate cholesterol esters in the low-density lipoprotein (ldl) particle. thus, 15-lox has been involved in the development of atherosclerosis, and cbdd may be a useful prototype for producing medicines for atherosclerosis [1].cbdd showed a potent inhibitory effect on the catalytic activity of cytochrome p450 2c19 with an ic50 value of 14.8 μμ [2]. cbdd inhibited the cyp2b6 activity with the ic50values of 75.7 μm [3]. cytochrome p450 enzymes have been isolated from numerous mammalian tissues such as liver, kidney, lung, intestine, adrenal cortex. cytochrome p450 enzymes have also existed in insects, plants, yeasts, and bacteria. cytochrome p450 has been known to catalyze hydroxylations, epoxidations, n-, s-, and o-dealkylations, n-oxidations, sulfoxidations, dehalogenations, and other reactions [4].
references
[1] takeda s, usami n, yamamoto i, et al. cannabidiol-2′, 6′-dimethyl ether, a cannabidiol derivative, is a highly potent and selective 15-lipoxygenase inhibitor[j]. drug metabolism and disposition, 2009, 37(8): 1733-1737.[2] jiang r, yamaori s, okamoto y, et al. cannabidiol is a potent inhibitor of the catalytic activity of cytochrome p450 2c19[j]. drug metabolism and pharmacokinetics, 2013, 28(4): 332-338.[3] yamaori s, maeda c, yamamoto i, et al. differential inhibition of human cytochrome p450 2a6 and 2b6 by major phytocannabinoids[j]. forensic toxicology, 2011, 29(2): 117-124.[4] groves j t, han y z. models and mechanisms of cytochrome p450 action[m]//cytochrome p450. springer us, 1995: 3-48.
Check Digit Verification of cas no
The CAS Registry Mumber 1242-67-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,4 and 2 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1242-67:
(6*1)+(5*2)+(4*4)+(3*2)+(2*6)+(1*7)=57
57 % 10 = 7
So 1242-67-7 is a valid CAS Registry Number.
InChI:InChI=1/C21H30O2.C2H6O/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3;1-3-2/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3;1-2H3/t17-,18+;/m0./s1
1242-67-7Relevant articles and documents
Synthesis of CBD and Its Derivatives Bearing Various C4′-Side Chains with a Late-Stage Diversification Method
Gong, Xudong,Sun, Changliang,Abame, Melkamu Alemu,Shi, Wenqiang,Xie, Yuanchao,Xu, Wanbin,Zhu, Fuqiang,Zhang, Yan,Shen, Jingshan,Aisa, Haji A.
, p. 2704 - 2715 (2020)
A novel synthetic route for making (-)-CBD and its derivatives bearing various C4′-side chains is developed by a late-stage diversification method. Starting from commercially available phloroglucinol, the key intermediate (-)-CBD-2OPiv-OTf is efficiently and regioselectively prepared and further undergoes Negishi cross-coupling to furnish (-)-CBD. This approach allowed an efficient synthesis of (-)-CBD in a five-step total 52% yield on a 10 g scale. Furthermore, diversification on the C4′-side chain with this method can be realized in a wide range.
Mechoulam,Gaoni
, p. 3273 (1965)
Synthetic method of cannabidiol
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Page/Page column 6-9, (2020/11/12)
The invention belongs to the field of chemical pharmacy, and particularly discloses a synthetic method of cannabidiol. The synthetic method comprises the following steps: S1, adopting 2, 4-dimethoxy-6-amyl methyl benzoate as a raw material, and carrying out a coupling reaction on the raw material and (1S, 4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-ol under a Lewis acid catalysis condition to obtain an intermediate (I); S2, performing high-temperature decarboxylation on the prepared intermediate (I) under the action of strong alkali to prepare an intermediate (II); and S3, removing methyl from the prepared intermediate (II) under the action of boron tribromide to obtain the final product cannabidiol. The purity of the cannabidiol obtained by the preparation method disclosed by the invention is 99.90-99.99%; the total yield of the finally prepared bulk drug with qualified purity can reach 60-80% at most, the process is obviously improved, and the method has a good industrial application prospect.
