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(L)-alpha-terpineol

HCID 443162
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Basic information

CAS
10482-56-1
Standard SMILES
CC1=CC[C@@H](C(C)(C)O)CC1
InChIKey
WUOACPNHFRMFPN-SECBINFHSA-N
Molecular formula
C10H18O
Average molar mass
154.25 g/mol
Monoisotopic mass
154.13576519

Overview

(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.

Names & identifiers

Preferred name
(L)-alpha-terpineol
IUPAC
2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-ol
English name
(-)-alpha-Terpineol
Molecular formula
C10H18O
Molecular weight
154.25

Names & synonyms

(-)-alpha-Terpineol(L)-alpha-Terpineol(S)-(-)-TerpineolL-alpha-TERPINEOL2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-olL-.alpha.-Terpineolalpha-TerpieolDTXSID5052672p-Menth-1-en-8-ol, (S)-(-)-alphaTerpineol, l.alpha.-Terpineol, (-)-HSDB 2683
Show more names
α-Terpineoll-α-Terpineolterpene alcohol(-)-α-Terpineol(S)-(-)-α-terpineol(S)-P-MENTH-1-EN-8-OLLilacinFEMA 3045
EINECS 233-986-83-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, (1S)-3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-, (S)-DTXCID2031245p-Menth-1-en-8-ol (S)-(-)-3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-, (1R)-3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-, (1S)-3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, (S)-

Database identifiers

CAS
10482-56-1、7785-53-7
PubChem CID
443162
DTXSID
DTXSID5052672
ChEMBL
CHEMBL447597
ChEBI
CHEBI:128
UNII
N9K6X87HU9
EC Number
233-986-8
Nikkaji
J9.809D

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
11
Formal charge
0
Complexity
168

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Plant Oils and Extracts
FragrancesFragrance Ingredient (p-Menth-1-en-8-ol (S)) -> IFRA transparency List
Density · 2 items

0.935 @ 20 °C/4 °C

0.935 @25 °C

Color/FormLiquid
Boiling Point · 2 items

80-81.5 °C @ 5 mm Hg

219 °C @760 [mm Hg]

Melting Point · 2 items

Solidifies @ 36.4 °C

33 °C

Vapor Pressure · 2 items

5 mm Hg @ 80 to 81 mm Hg

0.05 [mm Hg] @25 °C

Refractive IndexIndex of refraction: 1.4820 @ 20 °C/D; specific optical rotation: -100 deg @ 20 °C/D (c= 20 in alc)
Physical DescriptionLiquid; mp = 36.4 deg C; [HSDB] Colorless liquid; mp = 40-41 deg C; [MSDSonline]

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 · 5 items

This chemical does not meet GHS hazard criteria for 0.2% (3 of 1513) of reports.

Warning

H315 (99.8%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 1513 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: 3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, (S)-

REACH registered substance: 2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-ol (EC: 233-986-8)

alpha-Terpineol: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

Included in list of established contact allergens in humans; [EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] An eye and mucous membrane irritant; Can cause hemorrhagic gastritis and CNS depression after ingestion; Emergency treatment: Pine oil; [HSDB] An irritant; [Aldrich MSDS]

Hazard Classes and CategoriesSkin Irrit. 2 (99.8%)
Skin, Eye, and Respiratory Irritations...Terpineols are irritating to eyes and mucous membranes.

Safety & protection

Disposal Methods · 1 item

Chemistry & industry

Pharmacology

Absorption, Distribution and Excretion · 1 item

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).

Uses & manufacturing

Uses · 6 items

Used to make perfumes and soaps and as a solvent (for hydrocarbons, resins, cellulose esters, and ethers) and antiseptic; Also used in disinfectants, antioxidants, medicines, and flavorings; [HSDB]

Using Disinfectants or Biocides [Category: Clean]

PERFUMES; DENATURING FATS FOR SOAP MFR; ANTISEPTIC /ALPHA-TERPINEOL/

SOLVENT FOR HYDROCARBON MATERIALS; MUTUAL SOLVENT FOR RESINS & CELLULOSE ESTERS & ETHERS; DISINFECTANT /TERPINEOL/

ANTIOXIDANT; FLAVORING AGENT /TERPINEOL/

Perfume manufacturing; soap manufacturing; hydrocarbon solvent; solvent for resins, cellulose esters, and ethers; disinfectants; antioxidants; medicines; constituent of flavorings.

Methods of Manufacturing · 2 items

BY HEATING TERPIN HYDRATE WITH PHOSPHORIC ACID & DISTILLING, OR WITH DIL SULFURIC, USING AZEOTROPIC SEPARATION; FRACTIONAL DISTILLATION OF PINE OIL. OCCURS NATURALLY IN SEVERAL ESSENTAIL OILS. GRADES: TECHNICAL; PERFUMERY; EXTRA; PRIME; FCC. /TERPINEOL/

Extraction of essential oils, fractional distilation of pine oils, wood processing industry.

Use ClassificationFragrance Ingredients
General Manufacturing Information · 3 items

3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, (1R)-: ACTIVE

3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, (1S)-: ACTIVE

FEMA NUMBER 3045

Applications · 2 items

Related reactions

3 records
New reaction record
HRID 426576 reaction equation
HRID 426576As reactantuspto-grants-1979_10
HRID 1194903 reaction equation
HRID 1194903As reactantuspto-grants-1989_03
HRID 2301003 reaction equation
HRID 2301003As reactantuspto-grants-2002_12

Compound notes

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Other Experimental Properties
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/

Physicochemical properties

Melting point
31 · 31-35 °C(lit.)
Boiling point
217 · 217-218 °C(lit.)
Density
0.93 g/mL · 0.93 g/mL at 25 °C(lit.)
vapor pressure
2.79 Pa · 2.79Pa at 20℃
refractive index
20 · n20/D 1.482(lit.)
FEMA
3045 · 3045 | ALPHA-TERPINEOL
Flash point
193 °F · 193 °F
storage temp.
30 °C · Store below +30°C.
solubility
Chloroform (Sparingly), Methanol (Slightly)
form
Solid
pka
15.09 · 15.09±0.29(Predicted)
color
Colourless to Off-White Oil
Specific Gravity
0.934 · 0.934 (20/4℃)
Odor
100 % · at 100.00 %. lilac floral terpenic
Odor Type
terpenic
Water Solubility
2.23 g/L · 2.23g/L at 20℃
BRN
2325137 · 2325137
Major Application
flavors and fragrances
InChI
1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m1/s1
InChIKey
WUOACPNHFRMFPN-SECBINFHSA-N
SMILES
CC1=CC[C@@H](C(O)(C)C)CC1
LogP
2.25 at · 2.25 at 20℃
CAS DataBase Reference
10482 · 10482-56-1(CAS DataBase Reference)
FDA UNII
9 K6X87HU9 · N9K6X87HU9
NIST Chemistry Reference
a-Terpineol(10482-56-1)
EPA Substance Registry System
1 · 1-.alpha.-Terpineol (10482-56-1)
UNSPSC Code
12352104 · 12352104
NACRES
22 · NA.22
Symbol(GHS)
5 · GHS05
Signal word
Danger
Hazard statements
315 · H315-H318
Precautionary statements
264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P362+P364
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36-36/37/39
RIDADR
1230 · UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany
2 · 2
RTECS
6700000 · WZ6700000
TSCA
TSCA listed
HS Code
2906 · 2906 19 00
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
1 Skin · Eye Dam. 1Skin Irrit. 2
Hazardous Substances Data
10482 · 10482-56-1(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: 4300 mg/kg LD50 dermal Rat > 5000 mg/kg
REACH Registrations
Active

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.

Preventive Measures · 1 item

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.

Protective Action Criteria (PAC) · 3 items

15 [mg/m3]

170 [mg/m3]

1000 [mg/m3]

Toxicology

Ecotoxicity ValuesLC50 Rainbow trout 10-100 mg/l at 10 °C (96 hours) /Conditions of bioassay not specified/
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Natural Pollution Sources · 1 item

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/

Human Toxicity Excerpts · 2 items

/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.

Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ After iv pine oil to horses, marked histopathological changes were seen in lungs. Lesions are largely related to resp tract; mechanism of death is acute pulmonary edema. /Pine oil/
Environmental Water ConcentrationsKRAFT PULP MILL WASTE WATER RECEIVING SECONDARY TREATMENT IN AERATED LAGOON WAS EXAMINED: ALPHA-TERPINEOL WAS ALWAYS THE PREDOMINANT TERPENE IN THE EFFLUENT.
Antidote and Emergency Treatment · 2 items

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/

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
WZ6700000
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
2906 19 00
Toxicity
LD50 orally in Rabbit: 4300 mg/kg LD50 dermal Rat > 5000 mg/kg
risk_code
36/37/38
Signal word
Danger
Symbol(GHS)
GHS05
hazard_code
Xi
safety_code
26-36-36/37/39
Storage Class
11 - Combustible Solids
Hazard statements
H315-H318
REACH Registrations
Active
Hazard Classifications
Eye Dam. 1Skin Irrit. 2
Precautionary statements
P264-P280-P302+P352-P305+P351+P338-P332+P313-P362+P364
Hazardous Substances Data
10482-56-1(Hazardous Substances Data)

Uses(S)-α-Terpineol comes from the essential oil extracted from the leaves of Zanthoxylum ailanthoides Sieb. Et Zucc. collected from Guizhou which possesses anti-oxidant activities.

General Descriptionα-Terpineol is a monoterpene alcohol. It is one of the components responsible for the antifungal activity of Melaleuca alternifolia (tea tree) essential oil. It is also found in Origanum essential oil and Rosmarinus officinalis essential oil.

Upstream & downstream products

Upstream raw materials

dilute sulphuric acidTurpentine oilalpha-PineneTerpine hydrateSulfuric acid

Downstream products

Terpinyl acetateDihydroterpineol

Additional notes

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