Olivetol

Modify Date: 2024-01-02 19:19:45

Olivetol Structure
Olivetol structure
 Common Name Olivetol
CAS Number 500-66-3 Molecular Weight 180.243
Density 1.1±0.1 g/cm3 Boiling Point 313.3±12.0 °C at 760 mmHg
Molecular Formula C11H16O2 Melting Point 46-48ºC
MSDS Chinese USA Flash Point 148.8±14.2 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Olivetol


Olivetol is a naturally phenol found in lichens and produced by certain insects, acting as a competitive inhibitor of the cannabinoid receptors CB1 and CB2[3]. Olivetol also inhibits CYP2C19 and CYP2D6 activity, with IC50s of 15.3 μM, 7.21 μM and Kis of 2.71 μM, 2.87 μM, respectively[1][2].

 Names

Name olivetol
Synonym More Synonyms

 Olivetol Biological Activity

Description Olivetol is a naturally phenol found in lichens and produced by certain insects, acting as a competitive inhibitor of the cannabinoid receptors CB1 and CB2[3]. Olivetol also inhibits CYP2C19 and CYP2D6 activity, with IC50s of 15.3 μM, 7.21 μM and Kis of 2.71 μM, 2.87 μM, respectively[1][2].
Related Catalog
Target

IC50: 7.21 μM (CYP2D6)[2], 15.3 μM (CYP2C19)[1] Ki: 2.71 μM (CYP2C19)[1], 2.87 μM (CYP2D6)[2] CB1, CB2[3]

In Vitro Olivetol inhibits the (S)-mephenytoin 4'-hydroxylase activity of CYP2C19 activity with an IC50 of 15.3 μM and a Ki of 2.71 μM[1]. Olivetol also inhibits AMMC O-demethylase activity of recombinant CYP2D6 with an IC50 of 7.21 μM and a Ki of 2.87 μM[2]. Olivetol is a competitive inhibitor of the cannabinoid receptors CB1 and CB2[3].
References

[1]. Jiang R, et al. Cannabidiol is a potent inhibitor of the catalytic activity of cytochrome P450 2C19. Drug Metab Pharmacokinet. 2013;28(4):332-8.

[2]. Yamaori S, et al. Cannabidiol, a major phytocannabinoid, as a potent atypical inhibitor for CYP2D6. Drug Metab Dispos. 2011 Nov;39(11):2049-56.

[3]. James J. Carberry , et al. Composition of Olivetol and Method of Use to Reduce or Inhibit the Effects of Tetrahydrocannabinol in the Human Body. US20170143644A1

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 313.3±12.0 °C at 760 mmHg
Melting Point 46-48ºC
Molecular Formula C11H16O2
Molecular Weight 180.243
Flash Point 148.8±14.2 °C
Exact Mass 180.115036
PSA 40.46000
LogP 3.35
Vapour Pressure 0.0±0.7 mmHg at 25°C
Index of Refraction 1.547
Storage condition Refrigerator

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VH2880000
CHEMICAL NAME :
Resorcinol, 5-pentyl-
CAS REGISTRY NUMBER :
500-66-3
BEILSTEIN REFERENCE NO. :
0908277
LAST UPDATED :
199612
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C11-H16-O2
MOLECULAR WEIGHT :
180.27

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Human Lymphocyte
DOSE/DURATION :
150 umol/L
REFERENCE :
FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 36,1748,1977

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi:Irritant;
Risk Phrases R36/37/38
Safety Phrases S26-S36/39
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS VH2880000
HS Code 2907299090

 Synthetic Route

 Customs

HS Code 2907299090
Summary 2907299090 polyphenols; phenol-alcohols。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:5.5%。general tariff:30.0%

 Articles11

More Articles
¹H NMR and HPLC/DAD for Cannabis sativa L. chemotype distinction, extract profiling and specification.

Talanta 140 , 150-65, (2015)

The medicinal use of different chemovars and extracts of Cannabis sativa L. requires standardization beyond ∆9-tetrahydrocannabinol (THC) with complementing methods. We investigated the suitability of...

Preparation and evaluation of molecularly imprinted polymer of olivetol for solid phase extraction.

Se Pu 31(6) , 587-95, (2013)

Molecularly imprinted polymer (MIP) was synthesized by bulk polymerization, using olivetol as template molecule, methyl acrylic acid (MAA) as monomer, ethylene glycol dimethacrylate (EDMA) as crosslin...

Cannabidiol is a potent inhibitor of the catalytic activity of cytochrome P450 2C19.

Drug Metab. Pharmacokinet. 28(4) , 332-8, (2013)

The present study investigated the inhibitory effect of cannabidiol (CBD), a major constituent of marijuana, on the catalytic activity of cytochrome P450 2C19 (CYP2C19). (S)-Mephenytoin 4'-hydroxylase...

 Synonyms

1,3-Benzenediol, 5-pentyl-
MFCD00002293
5-pentylbenzene-1,3-diol
5-Pentyl-1,3-benzenediol
EINECS 207-908-8
Olivetol
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Related Compounds: More...
Olivetol-d9
137125-92-9
Olivetol-d7
1175096-29-3
dimethoxyolivetol
22976-40-5
5'-bromo olivetol
58545-34-9
Di-O-methylolivetol-d9
137125-91-8
olivetol/β-cyclodextrin complex
781642-49-7
Olivetol bis(tetrahydropyranylether)
71135-96-1
2-Methyl-2-<3,5-dihydroxy-phenyl>-hexan,1',1'-Dimethyl-olivetol
22930-09-2
Chemsrc provides Olivetol(CAS#:500-66-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Olivetol are included as well.>> amp version: Olivetol

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