Cannabielsoin
Basic information
- CAS
52025-76-0- Standard SMILES
C=C(C)[C@@H]1CC[C@](C)(O)[C@H]2Oc3cc(CCCCC)cc(O)c3[C@@H]12- InChIKey
RBEAVAMWZAJWOI-MTOHEIAKSA-N- Molecular formula
- C21H30O3
- Average molar mass
- 330.5 g/mol
- Monoisotopic mass
- 330.21949481
Overview
cannabielsoin has been reported in Cannabis sativa with data available.
Names & identifiers
- Preferred name
- Cannabielsoin
- IUPAC
- (5aS,6S,9R,9aR)-6-methyl-3-pentyl-9-prop-1-en-2-yl-7,8,9,9a-tetrahydro-5aH-dibenzofuran-1,6-diol
- English name
- cannabielsoin
- Molecular formula
- C21H30O3
- Molecular weight
- 330.46
Names & synonyms
CannabielsoinCannabielsoin A52025-76-02ERD6V6652(5aS,6S,9R,9aR)-6-methyl-3-pentyl-9-prop-1-en-2-yl-7,8,9,9a-tetrahydro-5aH-dibenzofuran-1,6-diolDTXSID509663641,6-Dibenzofurandiol, 5a,6,7,8,9,9a-hexahydro-6-methyl-9-(1-methylethenyl)-3-pentyl-, (5aS-(5aalpha,6alpha,9alpha,9aalpha))-RefChem:123225DTXCID70139400110-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo(7.4.0.02,7)trideca-2(7),3,5-triene-3,10-diolCBECANNABIELSOIN I
Show more names
Cannabielsoin (CRM)Cannabielsoin (CBE) solution(5aS,6S,9R)-5aβ,6,7,8,9,9aβ-Hexahydro-6α-methyl-9β-(1-methylethenyl)-3-pentyl-1,6-dibenzofurandiol1,6-Dibenzofurandiol, 5a,6,7,8,9,9a-hexahydro-6-methyl-9-(1-methylethenyl)-3-pentyl-, (5aS,6S,9R,9aR)-
(5as,6s,9r,9ar)-6-methyl-3-pentyl-9-(prop-1-en-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzo[b,d]furan-1,6-diolUNII-2ERD6V6652orb2299251SCHEMBL13214152SCHEMBL29351653RBEAVAMWZAJWOI-MTOHEIAKSA-NR21AT012695-Cannabinoid-017TN7522
Properties
Computed structural properties
- XLogP
- 5.4
- Topological polar surface area
- 49.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 462
Physicochemical properties
- Boiling point
- 426.5 · 426.5±45.0 °C(Predicted)
- Density
- 1.089 · 1.089±0.06 g/cm3(Predicted)
- storage temp.
- -10 to · -10 to -25°C
- solubility
- 50 mg/ml; · DMF: 50 mg/ml; DMSO: 60 mg/ml; DMSO:PBS (pH 7.2) (1:3): 0.25 mg; Ethanol: 35 mg/ml
- pka
- 9.78 · 9.78±0.60(Predicted)
- InChI
- 1S/C21H30O3/c1-5-6-7-8-14-11-16(22)19-17(12-14)24-20-18(19)15(13(2)3)9-10-21(20,4)23/h11-12,15,18,20,22-23H,2,5-10H2,1,3-4H3/t15-,18+,20-,21-/m0/s1
- InChIKey
- RBEAVAMWZAJWOI-MTOHEIAKSA-N
- SMILES
- O1[C@H]2[C@H]([C@@H](CC[C@@]2(O)C)C(=C)C)c3c1cc(cc3O)CCCCC
- FDA UNII
- 2 ERD6V6652 · 2ERD6V6652
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H301+H311+H331-H370
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Health Effects
CDFs cause vomiting and diarrhea, anemia, more frequent lung infections, numbness and other effects on the nervous system, and mild changes in the liver. However, there were no permanent liver changes or definite liver damage found in people who ingested CDFs. (L952)
Exposure RoutesInhalation (L952) ; dermal (L952) ; oral (L952)
Toxicity SummaryDibenzofurans bind the aryl hydrocarbon receptor, which increases its ability to activate transcription in the XRE promoter region. This alters the expression of a number of genes. (A586)
Signs and SymptomsSkin and eye irritations, especially severe acne, darkened skin color, and swollen eyelids with discharge are the most obvious health effects of the CDF poisoning. (L952)
Carcinogen ClassificationNo indication of carcinogenicity (not listed by IARC). (L135)
Safety data
- wgk
- WGK 2
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- Storage Class
- 3 - Flammable liquids
- target organs
- Eyes,Central nervous system
- Hazard statements
- H225-H301+H311+H331-H370
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- Precautionary statements
- P210-P233-P280-P301+P310-P303+P361+P353-P304+P340+P311
Chemistry & industry
Pharmacology
Metabolism/Metabolites
No information on the metabolism of dibenzofuran in mammalian organisms was found in the available literature. The bacteria Sphingomonas, Brevibacterium, Terrabacter, and Staphylococcus auricularis degrade dibenzofuran to 2,2',3-trihydroxybiphenyl via dibenzofuran 4,4a-dioxygenase. (L952)
Uses & manufacturing
UsesCDFs are created from production of coal tar and during incineration. They are used as insecticides, in the production of PVC, and in industrial bleaching. (L952)
Applications
DescriptionCannabielsoin (CRM) (Item No. 36661) is a certified reference material categorized as a phytocannabinoid metabolite.1,2 Cannabielsoin is a metabolite of cannabidiol (CBD; Item Nos. ISO60156 | 90080). This product is intended for research and forensic applications.WARNING This product is not for human or veterinary use.
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Compound notes
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