Olivetol

Names

[ CAS No. ]:
500-66-3

[ Name ]:
Olivetol

[Synonym ]:
1,3-Benzenediol, 5-pentyl-
MFCD00002293
5-pentylbenzene-1,3-diol
5-Pentyl-1,3-benzenediol
EINECS 207-908-8
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]:

Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Research Areas >> Neurological Disease

Natural Products >> Phenols

[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

[Related Small Molecules]

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

MSDS

Click to get detail MSDS

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

[ 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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%

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...