Olivetol
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Olivetol
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CAS No:
500-66-3
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Formula:
C11H16O2
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Chemical Name:
Olivetol
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Synonyms:
1,3-Benzenediol,5-pentyl-;Olivetol;Resorcinol,5-pentyl-;5-Pentyl-1,3-benzenediol;3,5-Dihydroxyamylbenzene;5-Pentylresorcinol;5-n-Amylresorcinol;5-n-Pentylresorcinol;1,3-Dihydroxy-5-pentylbenzene;5-Pentylbenzene-1,3-diol;3,5-Dihydroxy-1-pentylbenzene
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CAS No:
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].
Olivetol appears as off-white crystals or olive to light purple waxy solid. Forms monohydrate (melting point: 102-106°F). (NTP, 1992)
Olivetol appears as off-white crystals or olive to light purple waxy solid. Forms monohydrate (melting point: 102-106°F). (NTP, 1992)|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.
Characteristics
40.5
3.6
Olivetol appears as off-white crystals or olive to light purple waxy solid. Forms monohydrate (melting point: 102-106°F). (NTP, 1992)
1.1±0.1 g/cm3
41 °C
164 °C
>230 °F
1.547
less than 1 mg/mL at 66° F (NTP, 1992)
Refrigerator
Sensitive to air. Insoluble in water.
Phenols and Cresols
OLIVETOL is incompatible with acid chlorides, acid anhydrides and oxidizing agents. (NTP, 1992)
Safety Information
NONH for all modes of transport
3
36/37/38
26-36/39
VH2880000
Xi
Stable at room temperature in closed containers under normal storage and handling conditions. May discolor on exposure to light.
P261-P305 + P351 + P338
H315-H319-H335
This chemical is probably combustible. (NTP, 1992)
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
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. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)
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)
Drug Information
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. ACUTE/CHRONIC HAZARDS: This compound is a severe irritant to the skin, eyes, mucous membranes and upper respiratory tract. It is harmful if swallowed, inhaled or absorbed through the skin. When heated to decomposition it emits toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
5-pentyl-1,3-dihydroxybenzene
Olivetol Use and Manufacturing
A precursor in various syntheses of tetrahydrocannabinol.
Lipids -> Polyketides [PK] -> Phenolic lipids [PK15] -> Alkyl resorcinols and derivatives [PK1503]
Computed Properties
Molecular Weight:180.24
XLogP3:3.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:180.115029749
Monoisotopic Mass:180.115029749
Topological Polar Surface Area:40.5
Heavy Atom Count:13
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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