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152633

Sigma-Aldrich

Olivetol

95%

Synonym(s):

1,3-Dihydroxy-5-pentylbenzene, 3,5-Dihydroxyamylbenzene, 5-Pentylresorcinol

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About This Item

Linear Formula:
CH3(CH2)4C6H3-1,3-(OH)2
CAS Number:
500-66-3
Molecular Weight:
180.24
EC Number:
207-908-8
MDL number:
MFCD00002293
UNSPSC Code:
12352100
PubChem Substance ID:
24849242
NACRES:
NA.22

Assay

95%

form

solid

mp

46-48 °C (lit.)

SMILES string

CCCCCc1cc(O)cc(O)c1

InChI

1S/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3

InChI key

IRMPFYJSHJGOPE-UHFFFAOYSA-N

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Application

Olivetol was used as a template molecule in the synthesis of molecularly imprinted polymer (MIP). It was also used as an inhibitor of (S)-mephenytoin 4′-hydroxylase activity of recombinant CYP2C19.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 3 - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1B - STOT SE 1 Oral - STOT SE 2 Oral

Target Organs

Central nervous system,Blood, Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Fellermeier et al.
FEBS letters, 427(2), 283-285 (1998-06-02)
A new enzyme, geranylpyrophosphate:olivetolate geranyltransferase (GOT), the first enzyme in the biosynthesis of cannabinoids could be detected in extracts of young leaves of Cannabis sativa. The enzyme accepts geranylpyrophosphate (GPP) and to a lesser degree also nerylpyrophosphate (NPP) as a
M G Cascio et al.
British journal of pharmacology, 149(4), 431-440 (2006-09-06)
We have previously reported the development of CB-25 and CB-52, two ligands of CB1 and CB2 cannabinoid receptors. We assessed here their functional activity. The effect of the two compounds on forskolin-induced cAMP formation in intact cells or GTP-gamma-S binding
Yafeng Jin et al.
Se pu = Chinese journal of chromatography, 31(6), 587-595 (2013-09-26)
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 crosslinker, toluene and dodecanol as solvents. The resulted MIP was characterized by the equilibrium binding
E A Formukong et al.
The Journal of pharmacy and pharmacology, 40(2), 132-134 (1988-02-01)
Tetrahydrocannabinol (THC) induced catalepsy in mice, whereas a cannabis oil (6.68% w/w THC), four cannabinoids and a synthetic mixture did not. Cannabinol (CBN) and olivetol inhibited THC-induced catalepsy in the mornings and the evenings, but cannabidiol (CBD) exhibited this effect
E A Formukong et al.
Inflammation, 12(4), 361-371 (1988-08-01)
Two extracts of Cannabis sativa herb, one being cannabinoid-free (ethanol) and the other containing the cannabinoids (petroleum), were shown to inhibit PBQ-induced writhing in mouse when given orally and also to antagonize tetradecanoylphorbol acetate (TPA)-induced erythema of mouse skin when
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