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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK3927
MKCJ9089
MKCJ5839
MKCG1427
MKBZ9024V

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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
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
Rongrong Jiang et al.
Drug metabolism and pharmacokinetics, 28(4), 332-338 (2013-01-16)
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 activities of human liver microsomes (HLMs) and recombinant CYP2C19 were inhibited by CBD in
R H McClanahan et al.
Journal of natural products, 47(5), 828-834 (1984-09-01)
A study of the biotransformation of olivetol by Syncephalastrum racemosum ATCC 18192 has led to the isolation of three metabolites, which were identified as 4'-hydroxy-olivetol, 3-(3,5-dihydroxyphenyl)-1-propanol, and 3-(3,5-dihydroxyphenyl)-1-propanoic acid. The structures of the isolated metabolites were deduced by comparison of
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