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55824-13-0

  • Product Name:CBDP
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Purity:99%

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55824-13-0 Name

Name

CBDP

Synonym

 1,3-Benzenediol, 5-heptyl-2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-, 5-Heptyl-2-[(1R,6R)-6-isopropenyl-3-methyl-2-cyclohexen-1-yl]-1,3-benzenediol

 

55824-13-0 Chemical & Physical Properties

Boiling point

488.1±45.0 °C at 760 mmHg

Density

1.0±0.1 g/cm3

Molecular Formula

C23H34O2

Molecular Weight

342.515

Flash Point

 212.6±23.3 °C

LogP

8.10

Exact Mass

342.255890

Vapour Pressure

0.0±1.3 mmHg at 25°C

Index of Refraction

1.538

A novel phytocannabinoid was named cannabidiphorol (CBDP) isolated from Cannabis sativa, which is a CBD homolog with a seven-term side alkyl chain. THCP and CBDP, has given the opportunity to study their distribution in cannabis germplasm.

 

CBDP 55824-13-0 Relevant articles

Using (+)-carvone to access novel derivatives of (+)-ent-cannabidiol: The first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV

Alexandra E. Golliher , Antonio J. Tenorio , Nina O. Dimauro , Nicolas R. Mairata , F. Omar Holguin , William Maio

Tetrahedron Letters Volume 67, 16 March 2021, 152891

Our interest in these latter two derivatives stems from structure activity relationship data that demonstrate the importance of the alkyl chain length and how these derivatives may bind to CB1 and CB2 receptors . Also of note, natural (−)-CBDV is in early clinical development for the treatment of autism spectrum disorders and recently, (−)-CBDP has emerged as a more potent cannabinoid than (−)-CBD itself, making it an alternative to THC therapy without the signature psychoactivity of the latter

C1′-cycloalkyl side chain pharmacophore in tetrahydrocannabinols

Papahatjis, Demetris P.,Nahmias, Victoria R.,Nikas, Spyros P.,Andreou, Thanos,Alapafuja, Shakiru O.,Tsotinis, Andrew,Guo, Jianxin,Fan, Pusheng,Makriyannis, Alexandros

, p. 4048 - 4060 (2008/02/09)

In earlier work we have provided evidence for the presence of a subsite within the CB1 and CB2 cannabinoid receptor binding domains of classical cannabinoids. However, these affinities are significantly improved with the introduction of a C2′-C3′ cis double bond that modifies the available conformational space within the side chain and allows for a better accommodation of a six-membered ring within the side chain subsite. Our SAR results are highlighted by molecular modeling of key analogs.

CBDP 55824-13-0 Process route

spherophorol
500-67-4

spherophorol

(1S,4R)-p-mentha-2,8-dien-1-ol
22972-51-6

(1S,4R)-p-mentha-2,8-dien-1-ol

5-heptyl-2-((1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl)benzene-1,3-diol
55824-13-0

5-heptyl-2-((1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl)benzene-1,3-diol

Conditions
Conditions Yield
With toluene-4-sulfonic acid; In benzene; at 10 - 20 ℃;
32%
3,5-dimethoxy-1-(1-heptenyl)benzene
23815-39-6

3,5-dimethoxy-1-(1-heptenyl)benzene

5-heptyl-2-((1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl)benzene-1,3-diol
55824-13-0

5-heptyl-2-((1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl)benzene-1,3-diol

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 95 percent / H2 / Pd/C / ethyl acetate / 20 °C
2: 91 percent / BBr3 / CH2Cl2 / -78 - 0 °C
3: 32 percent / p-toluenesulfonic acid / benzene / 10 - 20 °C
With hydrogen; boron tribromide; toluene-4-sulfonic acid; palladium on activated charcoal; In dichloromethane; ethyl acetate; benzene;
 

55824-13-0 Upstream products

  • 500-67-4
    500-67-4

    spherophorol

  • 22972-51-6
    22972-51-6

    (1S,4R)-p-mentha-2,8-dien-1-ol

  • 23815-39-6
    23815-39-6

    3,5-dimethoxy-1-(1-heptenyl)benzene

  • 6121-64-8
    6121-64-8

    5-n-heptyl resorcinol dimethyl ether

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