Cannabielsoin(CBE) (CAS 52025-76-0) is a phytocannabinoid derivative with potential analgesic and neuroprotective applications. Its structural complexity and lipophilicity present challenges in drug development but also offer opportunities for targeted therapeutic formulations.
Name :
CannabielsoinCAS No. :
52025-76-0MF :
C₂₁H₃₀O₃MW :
330.46Purity :
95%Appearance :
White to off-white crystalline solid .Storage Condition :
-20°C for long-term stability, Protect from light and moisture.Basic Information
Chemical Name: (5aS,6S,9R,9aR)-5a,6,7,8,9,9a-Hexahydro-6-methyl-9-(1-methylethenyl)-3-pentyl-1,6-dibenzofurandiol
CAS Number: 52025-76-0
Molecular Formula: C₂₁H₃₀O₃
Molecular Weight: 330.46 g/mol
Synonyms:
Cannabielsoin A
Cannabielsoin I
1,6-Dibenzofurandiol, 5a,6,7,8,9,9a-hexahydro-6-methyl-9-(1-methylethenyl)-3-pentyl-
CBE
Chemical Structure
Core Structure: A hexahydrodibenzo[b,d]furan derivative with a pentyl side chain and a methyl group at position 6.
Functional Groups:
Two phenolic hydroxyl (-OH) groups at positions 1 and 6.
A double bond (C=C) at position 9.
Stereochemistry: Four chiral centers (5aS, 6S, 9R, 9aR) confirmed by X-ray crystallography .
Physical and Chemical Properties
Appearance: White to off-white crystalline solid .
Melting Point: Not explicitly reported, but likely decomposes above 300°C.
Boiling Point: 426.5°C (predicted at 760 mmHg) .
Density: 1.089 g/cm³ (predicted) .
Solubility:
Poorly soluble in water (<1 mg/mL).
Moderately soluble in organic solvents (ethanol: 35 mg/mL, DMSO: 60 mg/mL).
LogP: 4.71 (highly lipophilic).
Key Applications
Pharmacological Activity:
Cannabinoid Receptor Modulation: Binds to CB₁ and CB₂ receptors with moderate affinity, exhibiting analgesic and anti-inflammatory effects .
Antioxidant Properties: Reduces oxidative stress in preclinical models.
Research Use:
Investigated for neuroprotective effects in neurodegenerative diseases.
Explored in combination therapies with THC/CBD for chronic pain management.
Safety and Handling
Toxicity:
Acute toxicity data unavailable; classified as "Harmful if swallowed" (H303) based on structural similarity to other cannabinoids .
Requires PPE (gloves, goggles) during handling.
Storage:
Store at -20°C for long-term stability .
Protect from light and moisture.
Synthesis and Production
Synthesis Routes:
Hydroxylation of CBV (Cannabivarin): Enzymatic or chemical modification to introduce hydroxyl groups.
Biocatalytic Methods: Use of microbial enzymes for selective functionalization.
Purification: Recrystallization from ethanol or column chromatography .
FAQ
Q1: What is Cannabielsoin (CBE) and how is it related to CBD?
A: Cannabielsoin (CBE) is a oxidative metabolite of Cannabidiol (CBD). It is formed through a specific enzymatic or photochemical cyclization reaction, making it a minor cannabinoid of interest in pharmacokinetic and metabolic studies.
Q2: Does CBE have psychoactive effects like THC?
A: No. Current research indicates that CBE is non-psychoactive. Its structure and mechanism of action are distinct from THC, and it does not bind significantly to the CB1 receptor responsible for the psychoactive effects of cannabis.
Q3: What is the main research interest in this compound?
A: Primary research focuses on its potential bioactive properties, which may include anti-inflammatory, neuroprotective, or anti-anxiety effects. It is also studied as a metabolic marker for CBD consumption and biodegradation.
Q4: What is the typical purity available and how should it be stored?
A: It is typically available as a solid or in solution at high purity grades (e.g., >95% by HPLC). For stability, it should be stored sealed under inert gas (N₂ or Argon) at low temperatures (-20°C) and protected from light to prevent degradation.
Q5: Is Cannabielsoin considered a controlled substance?
A: The legal status of minor cannabinoids varies by jurisdiction. While often not explicitly listed, it may be considered an analog of CBD or THC under broader laws. It is the customer's responsibility to verify the regulatory status in their region prior to purchase.
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Cannabielsoin(CBE) (CAS 52025-76-0) is a phytocannabinoid derivative with potential analgesic and neuroprotective applications. Its structural complexity and lipophilicity present challenges in drug development but also offer opportunities for targeted therapeutic formulations.
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