Cannabielsoin
(Synonyms: Cannabielsoin A, Cannabielsoin I, CBE) 目录号 : GC47026
An Analytical Reference Standard
Cas No.:52025-76-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cannabielsoin is an analytical reference standard categorized as a phytocannabinoid metabolite.1,2 Cannabielsoin is a metabolite of cannabidiol . This product is intended for research and forensic applications.
1.Yamamoto, I., Gohda, H., Narimatsu, S., et al.Identification of cannabielsoin, a new metabolite of cannabidiol formed by guinea-pig hepatic microsomal enzymes, and its pharmacological activity in miceJ. Pharmacobiodyn.11833-838(1988) 2.Yamamoto, I., Gohda, H., Narimatsu, S., et al.Cannabielsoin as a new metabolite of cannabidiol in mammalsPharmacol. Biochem. Behav.40(3)541-546(1991)
| Cas No. | 52025-76-0 | SDF | |
| 别名 | Cannabielsoin A, Cannabielsoin I, CBE | ||
| Canonical SMILES | OC1=C2C(O[C@@]3([H])[C@]2([H])[C@H](C(C)=C)CC[C@@]3(O)C)=CC(CCCCC)=C1 | ||
| 分子式 | C21H30O3 | 分子量 | 330.5 |
| 溶解度 | DMF: 50 mg/ml,DMSO: 60 mg/ml,DMSO:PBS (pH 7.2) (1:3): 0.25 mg,Ethanol: 35 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0257 mL | 15.1286 mL | 30.2572 mL |
| 5 mM | 0.6051 mL | 3.0257 mL | 6.0514 mL |
| 10 mM | 0.3026 mL | 1.5129 mL | 3.0257 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Structural revision of a Wnt/β-catenin modulator and confirmation of Cannabielsoin constitution and configuration
Chem Commun (Camb) 2021 Jun 8;57(46):5658-5661.PMID:33972980DOI:10.1039/d1cc01971f.
In this report, we revise the structure for a previously reported synthetic product proposed to be the 1R,2S-cannabidiol epoxide and reassign it as Cannabielsoin using anisotropic NMR and synthetic chemistry methods. These results provide a direct link to the first known biological target and function of Cannabielsoin.
Cannabielsoin as a new metabolite of cannabidiol in mammals
Pharmacol Biochem Behav 1991 Nov;40(3):541-6.PMID:1806944DOI:10.1016/0091-3057(91)90360-e.
Cannabielsoin (CBE) was identified as a novel metabolite of cannabidiol (CBD) in the guinea pig in vivo and in vitro. Its formation by liver microsomes of guinea pigs needed NADPH and molecular oxygen, and was inhibited with SKF 525-A, metyrapone and alpha-naphthoflavone, indicating participation of cytochrome P-450 (P-450). The CBE-forming activity was highest in guinea pigs, followed by mice, rabbits and rats. In the rat, sex difference was found in the CBE formation (male greater than female). CBD monomethylether (CBDM) was also biotransformed to CBE monomethylether (CBEM) in the guinea pig in vivo and in vitro. When CBD dimethylether (CBDD) was employed as substrate, 1S,2R-epoxy-CBDD was identified. The results suggest that CBD and CBDM are biotransformed by P-450 to CBE-type metabolites via 1S,2R-epoxides. In pharmacological studies using mice, CBDD and 1S,2R-epoxy-CBD-2',6'-diacetate produced hypothermia, and CBD, CBDM and CBEM prolonged pentobarbital-induced sleep. Moreover, 1S,2R-epoxy-CBD-2',6'-diacetate was examined in the Ames test, but had no mutagenicity.
Biotransformation of Cannabidiol to Cannabielsoin by Suspension Cultures of Cannabis sativa and Saccharum officinarum
Planta Med 1983 May;48(1):17-9.PMID:17404934DOI:10.1055/s-2007-969870.
Suspension cultures of CANNABIS SATIVA L. and SACCHARUM OFFICINARUM L. have been shown to biotransform cannabidiol to Cannabielsoin under normal growth conditions. Both Cannabielsoin C-1 stereoisomers were produced. Mass spectral and chromatographic evidence were used in this identification. This is the first reported biologically catalyzed synthesis of Cannabielsoin as well as the first biotransformation of any cannabinoid by plant tissue culture systems. Possible mechanisms and significance of this conversion are discussed.
Mechanism of biological formation of Cannabielsoin from cannabidiol in the guinea-pig, mouse, rat and rabbit
J Pharmacobiodyn 1989 Aug;12(8):488-94.PMID:2614640DOI:10.1248/bpb1978.12.488.
Biological formation of Cannabielsoin (CBE) from cannabidiol (CBD) was studied in the guinea pig, mouse, rat and rabbit in vitro. Emphasis was placed on the elucidation of this formation mechanism. The enzyme activity of CBE formation was localized in hepatic microsomes. The enzymatic reaction required nicotinamide adenine dinucleotide phosphate (NADPH) and molecular oxygen, and showed an optimal pH around 7.3. The microsomal CBE-forming activities decreased in the following order; guinea pig greater than mouse greater than or equal to rabbit greater than or equal to rat. The CBE formation in the guinea pig hepatic microsomes was suppressed with various inhibitors of cytochrome P-450 such as SKF 525-A, alpha-naphthoflavone and carbon monoxide, but not by disodium ethylenediamine tetraacetate. When incubated with the microsomes either in the presence or absence of NADPH, a synthetic epoxide of CBD, 1S, 2R-epoxy-CBD-2',6'-diacetate was easily and exclusively converted to CBE. On the other hand, 1R, 2S-epoxy-CBD was not changed to CBE at all, but to several oxidized metabolites. These results suggest that CBD is biotransformed to 1S,2R-epoxy-CBD with hepatic microsomal monooxygenase system including cytochrome P-450, and the epoxide is immediately converted to CBE.
Identification of Cannabielsoin, a new metabolite of cannabidiol formed by guinea-pig hepatic microsomal enzymes, and its pharmacological activity in mice
J Pharmacobiodyn 1988 Dec;11(12):833-8.PMID:3254981DOI:10.1248/bpb1978.11.833.
Metabolism of cannabidiol (CBD), one of the major components of marihuana, was studied in the guinea pig both in vitro and in vivo. Analyses of metabolites by gas chromatography and gas chromatography-mass spectrometry proved that Cannabielsoin (CBE) was formed from CBD as a novel metabolite, and that the amount was about one-sixth of 7-hydroxy-CBD, which was the most abundant metabolite under in vitro conditions in the presence of microsomal monooxygenase (cytochrome P-450). CBE was also found in the liver of the guinea pig that was given CBD (100 mg/kg) intraperitoneally 1 h before sacrifice. The effects of CBE on pentobarbital-induced sleep and body temperature were assessed in the mouse; CBE possessed little activity in either case.