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Home > Encyclopedia > (-)-α-Terpineol

(-)-α-Terpineol

(-)-α-Terpineol structure

(-)-α-Terpineol 

structure
  • CAS No:

    10482-56-1

  • Formula:

    C10H18O

  • Chemical Name:

    (-)-α-Terpineol

  • Synonyms:

    3-Cyclohexene-1-methanol,α,α,4-trimethyl-,(1S)-;p-Menth-1-en-8-ol,(S)-(-)-;3-Cyclohexene-1-methanol,α,α,4-trimethyl-,(S)-;(1S)-α,α,4-Trimethyl-3-cyclohexene-1-methanol;l-α-Terpineol;(-)-α-Terpineol;α-Terpineol,(-)-;(S)-α-Terpineol;(S)-(-)-α-Terpineol;(S)-(-)-Terpineol;(S)-α,α,4-Trimethyl-3-cyclohexene-1-methanol;2-[(1S)-4-Methylcyclohex-3-en-1-yl]propan-2-ol

  • Categories:

    Organic Chemistry  >  Alcohols, Phenols, Phenol Alcohols

Description

ChEBI: The (S)-enantiomer of alpha-terpineol.


(S)-(-)-alpha-terpineol is the (S)-enantiomer of alpha-terpineol. It has a role as a plant metabolite. It is an enantiomer of a (R)-(+)-alpha-terpineol.

(-)-α-Terpineol Basic Attributes

154.25

154.25

233-986-8

N9K6X87HU9

DTXSID5052672

Liquid

2906 19 00

Characteristics

20.2

2.79

Clear, colorless liquid.

0.935 g/cm3 @ Temp: 20 °C

33 °C

80-81.5 °C @ Press: 5 Torr

193 °F

n 20/D 1.482(lit.)

2-8°C

5 mm Hg @ 80 to 81 mm Hg

LD50 orally in Rabbit: 4300 mg/kg LD50 dermal Rat > 5000 mg/kg

BP: 81-82 °C @ 4.5 mm Hg; density: 0.9338 @ 20 °C/4 °C; index of refraction: 1.4818; specific optical rotation: +92.45 deg @ 20 °C/D; solidifies @ 31 °C /d-Form/

Safety Information

UN1230 - class 3 - PG 2 - Methanol, solution

2

36/37/38

26-36-36/37/39

WZ6700000

Xi

Stable under normal temperatures and pressures.

P305 + P351 + P338

H315-H319

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 1543 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

...Terpineols are irritating to eyes and mucous membranes.

Toxicity

L-FORM IS FOUND IN SATUREIA MONTANA, LAVANDIN, CAJEPUT, LIME, LEMON, CINNAMON LEAVES, & DISTILLATES FROM PINACEAE (WITH THE EXCEPTION OF PINUS SILVESTRIS, WHICH CONTAINS D-TERPINEOL TOGETHER WITH THE RACEMIC FORM); LIKEWISE, NECTANDRA ELAIOPHORA (WOOD) & PETITGRAIN BIGARADE. /L-ISOMER/

KRAFT PULP MILL WASTE WATER RECEIVING SECONDARY TREATMENT IN AERATED LAGOON WAS EXAMINED: ALPHA-TERPINEOL WAS ALWAYS THE PREDOMINANT TERPENE IN THE EFFLUENT.

Drug Information

3. 3= MODERATLY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB). /TERPINEOLS/

AFTER LETHAL IV PINE OIL 0.1 ML/KG TO HORSE, BLOOD & TISSUE LEVELS OF ALPHA-TERPINEOL 150-300 PPM WERE OBSERVED. AFTER SMALLER PINE OIL DOSES (0.033 ML/KG) BLOOD LEVELS BECAME UNDETECTABLE AFTER 2 HR, & NO TISSUE LEVELS DETECTED (TIME NOT SPECIFIED).

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. /Turpentine, terpenes, and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Turpentine, Terpenes, and related compounds/

/HUMAN EXPOSURE STUDIES/ ...Terpineols are irritating to eyes and mucous membranes. Produce hemorrhagic gastritis when ingested. Systemic effects incl weakness and central nervous depression, with hypothermia and resp failure. /Terpineols/|/CASE REPORTS/ The case history and toxicological findings of a fatal PineSol intoxication are presented. An 89-yr-old white female with Alzheimer's disease accidentally drank PineSol and was subsequently brought to the hospital where she was pronounced dead on arrival. Significant autopsy findings included acute erosive gastritis. There appeared to be no aspiration of PineSol into the lungs. Isopropanol along with 1-alpha-terpineol are the two major toxic ingredients of PineSol. ...Postmortem blood, urine, and gastric levels of 1-alpha-terpineol were 11.2 mg/l, 5.76 mg/l, and 15.3 g/l, respectively. Postmortem blood, vitreous humor, urine, and gastric acetone concns were 25, 31, 33, and 28 mg/dl. Postmortem concns of isopropanol were <10 mg/dl in the blood, vitreous humor, urine, and gastric contents. The cause of death was ruled acute 1-alpha-terpineol intoxication due to accidental ingestion of PineSol, presumably caused by confusion related to Alzheimer's disease.

1-alpha-terpineol

(-)-α-Terpineol Use and Manufacturing

Methods of Manufacturing

Treat turpentine with 23% dilute sulfuric acid to transform the main component α-pinene into terpene diol monohydrate. This intermediate is dehydrated to obtain crude terpineol, which is then fractionated and refined to produce refined products. Raw material consumption quota: 1, 730kg/t of turpentine, 650kg/t of sulfuric acid (98%), and 160kg/t of caustic soda.

Uses

Used in pharmaceutical industry, also used as fragrance, solvent and ink, etc.

3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, (1S)-: ACTIVE|FEMA NUMBER 3045

AFTER IV PINE OIL INJECTION, ALPHA TERPINEOL RECOVERED FROM EQUINE TISSUES BY EXTRACTION INTO HEPTANE & GC DETECTION, USING EITHER FLAME IONIZATION DETECTION OR PENTAFLUOROPROPIONIC ANHYDRIDE DERIVATIZATION & ELECTRON CAPTURE DETECTION.

Computed Properties

Molecular Weight:154.25
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:154.135765193
Monoisotopic Mass:154.135765193
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:168
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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