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Olivetol

HCID 10377
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Basic information

CAS
500-66-3
Standard SMILES
CCCCCc1cc(O)cc(O)c1
InChIKey
IRMPFYJSHJGOPE-UHFFFAOYSA-N
Molecular formula
C11H16O2
Average molar mass
180.24 g/mol
Monoisotopic mass
180.11502975

Overview

Olivetol appears as off-white crystals or olive to light purple waxy solid. Forms monohydrate (melting point: 102-106 °F). (NTP, 1992)

Names & identifiers

Preferred name
Olivetol
IUPAC
5-pentylbenzene-1,3-diol
English name
Olivetol
Molecular formula
C11H16O2
Molecular weight
180.24

Names & synonyms

OLIVETOL500-66-35-pentylbenzene-1,3-diol5-Pentylresorcinol5-Pentyl-1,3-benzenediol3,5-Dihydroxyamylbenzene5-n-Amylresorcinol5-n-Pentylresorcinol1,3-Benzenediol, 5-pentyl-Resorcinol, 5-pentyl-DTXSID002581265OP0NEZ1P
Show more names
Olivetol PowderCL213ivetoLOlidolOilvetol
5-pentyl-1,3-dihydroxybenzeneCHEBI:66960DTXCID205812RefChem:856753207-908-81,3-Dihydroxy-5-pentylbenzeneMFCD00002293CCRIS 6084

Database identifiers

CAS
500-66-3
PubChem CID
10377
DTXSID
DTXSID0025812
ChEMBL
CHEMBL154533
ChEBI
CHEBI:66960
UNII
65OP0NEZ1P
EC Number
207-908-8
Nikkaji
J11.681E

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
40.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
4
Heavy atoms
13
Formal charge
0
Complexity
126

Experimental & physicochemical properties

LipidsLipids -> Polyketides [PK] -> Phenolic lipids [PK15] -> Alkyl resorcinols and derivatives [PK1503]
Solubilityless than 1 mg/mL at 66 °F (NTP, 1992)
Flash Pointgreater than 230 °F (NTP, 1992)
Boiling Point327 °F at 5 mmHg (NTP, 1992)
Melting Point120 °F (NTP, 1992)
Physical DescriptionOlivetol appears as off-white crystals or olive to light purple waxy solid. Forms monohydrate (melting point: 102-106 °F). (NTP, 1992)
Collision Cross Section148.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID0025812]

Physicochemical properties

Melting point
46 · 46-48 °C(lit.)
Boiling point

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information1,3-Benzenediol, 5-pentyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health Hazards · 1 item

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Depending on the intensity and duration of exposure, effects may vary from mild irritation to severe destruction of tissue. Prolonged contact can cause damage to the eyes, severe irritation or burns.

Reactive GroupPhenols and Cresols
Reactivity ProfileOLIVETOL is incompatible with acid chlorides, acid anhydrides and oxidizing agents. (NTP, 1992)
Air and Water ReactionsSensitive to air. Insoluble in water.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Chemistry & industry

Applications

UsesOlivetol 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.

General DescriptionOlivetol appears as off-white crystals or olive to light purple waxy solid. Forms monohydrate (melting point: 102-106°F). (NTP, 1992)

Preparation methods

Preparationolivetol can also be formed through hydrolysis of intermediate polyketide CoAs or spontaneous cyclization.

Upstream & downstream products

Upstream raw materials

3-Nonen-2-oneSodium dithioniteAcetoneSodiumBromineAcetic acidDiethyl malonatePyridineHexanalBenzenemethanol, α-butyl-3,5-bis(phenylmethoxy)-3,5-Bis(benzyloxy)benzoic acid benzyl estermethyl 6-n-pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylatemethyl 2,4-dihydroxy-6-pentylbenzoate

Related reactions

26 records
New reaction record
HRID 159745 reaction equation
HRID 159745As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 204309 reaction equation
HRID 204309As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 268120 reaction equation
HRID 268120As reactantuspto-grants-1976_03
HRID 268122 reaction equation
HRID 268122As reactantuspto-grants-1976_03
HRID 391351 reaction equation
HRID 391351As reactantuspto-grants-2013_02
HRID 435139 reaction equation
HRID 435139As reactantuspto-grants-1983_08
HRID 443630 reaction equation
HRID 443630As reactantuspto-grants-1981_04
HRID 488670 reaction equation
HRID 488670As reactantuspto-grants-2005_12
Page 1 of 4

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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164 °C · 164 °C
Density
1.068 · 1.068±0.06 g/cm3(Predicted)
Flash point
230 °F · >230 °F
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Solid
pka
9.59 · 9.59±0.10(Predicted)
color
Colourless to Beige
Stability
Light Sensitive
InChI
InChI=1S/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3
InChIKey
IRMPFYJSHJGOPE-UHFFFAOYSA-N
SMILES
C1(O)=CC(CCCCC)=CC(O)=C1
CAS DataBase Reference
500 · 500-66-3(CAS DataBase Reference)
FDA UNII
65 OP0NEZ1P · 65OP0NEZ1P
NIST Chemistry Reference
1 · 1,3-Benzenediol, 5-pentyl-(500-66-3)
EPA Substance Registry System
Olivetol (500-66-3)
UNSPSC Code
12352100 · 12352100
NACRES
24 · NA.24
Symbol(GHS)
5 · GHS05,GHS07,GHS09
Signal word
Danger
Hazard statements
302 · H302-H315-H318-H400
Precautionary statements
273 · P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310
target organs
Central nervous system,Blood, Respiratory system
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36/39
WGK Germany
3 · 3
RTECS
2880000 · VH2880000
HS Code
2907299090 · 2907299090
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 3Eye Dam. 1Skin Irrit. 2Skin Sens. 1BSTOT SE 1 OralSTOT SE 2 Oral

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
VH2880000
hs_code
2907299090
risk_code
36/37/38
Signal word
Danger
Symbol(GHS)
GHS05,GHS07,GHS09
hazard_code
Xi
safety_code
26-36/39
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
target organs
Central nervous system,Blood, Respiratory system
Hazard statements
H302-H315-H318-H400
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 3Eye Dam. 1Skin Irrit. 2Skin Sens. 1BSTOT SE 1 OralSTOT SE 2 Oral
Precautionary statements
P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310
3,5-Dibenzyloxybenzyl alcohol
Olivetol Dimethyl Ether
3,5-Dibenzyloxybenzaldehyde
3,5-Dihydroxybenzoic acid
3,5-Dimethoxybenzoyl chloride

Additional notes

DefinitionChEBI: Olivetol is a member of the class of resorcinols that is resorcinol in which the hydrogen at position 5 is replaced by a pentyl group. It has a role as a lichen metabolite.