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(+)-Menthol

HCID 165675
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Grundinformationen

CAS
15356-60-2
Standard-SMILES
CC(C)[C@H]1CC[C@H](C)C[C@@H]1O
InChIKey
NOOLISFMXDJSKH-AEJSXWLSSA-N
Summenformel
C10H20O
Durchschnittliche Molmasse
156,26 g/mol
Monoisotopische Masse
156,15141526

Überblick

D,l-menthol is a white crystalline solid with a peppermint odor and taste. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
(+)-Menthol
IUPAC
(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-ol
Lokaler Name
(+)-Menthol
Englischer Name
(+)-MENTHOL
Summenformel
C10H20O
Molmasse
156.27

Namen und Synonyme

(+)-Menthol15356-60-2d-Menthol(1S,2R,5S)-(+)-Menthol(1S,2R,5S)-Menthol(1S,2R,5S)-2-Isopropyl-5-methylcyclohexanolCyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)-Menthol, (+)-DTXSID8029733C6B1OE8P3WMenthol, (1S,3S,4R)-(+)-(+)-(1S,2R,5S)-menthol
Weitere Namen anzeigen
C00553(1S,2R,5S)-dextro-mentholD-P-MENTHAN-3-OL(1S)-(+)-menthol(+)-p-Menthan-3-ol(+)-Menthol solution
(+)-(1S,3S,4R)-mentholEINECS 239-387-8MENTHOL, D-DTXCID409733CHEBI:76306EC 239-387-8Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S-(1alpha,2beta,5alpha))-Cryomax Cooling

Datenbank-Bezeichner

CAS
15356-60-2、15356-70-4、89-78-1
PubChem CID
165675
DTXSID
DTXSID8029733
ChEMBL
CHEMBL2106989、CHEMBL41763
ChEBI
CHEBI:76306
UNII
C6B1OE8P3W
EC Number
239-387-8、239-388-3
Nikkaji
J9.252E

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
3
Polarare Oberfläche (TPSA)
20,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
1
Schwere Atome
11
Formalladung
0
Komplexität
120

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Plant Oils and Extracts
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsCosmetics ingredient -> Buffering/pH Adjusting; Conditioning/Emollient; Flavor; Fragrance; Other (Specify)
SpringerMaterials PropertiesOptical coefficient
FragrancesFragrance Ingredient (d-Menthol) -> IFRA transparency List
Density · 2 Einträge

0.904 at 59 °F (NTP, 1992) - Less dense than water; will float

0.901 (20 °C); 0.891 (30 °C)

Solubility · 3 Einträge

less than 1 mg/mL at 70 °F (NTP, 1992)

very soluble in alcohol and volatile oils; slightly soluble in water

(in ethanol)

Flash Point196 °F (NTP, 1992)
Boiling Point · 2 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1451) of reports.

Warning

H315 (> 99.9%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 1451 reports by companies from 5 notifications to the ECHA C&L Inventory.

Danger

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel-

Chemical: Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1S-(1.alpha.,2.beta.,5.alpha.)]-

Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 13-10-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/12128

Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety Information · 2 Einträge

IMAP assessments - Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel-: Human health tier I assessment

IMAP assessments - Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1S-(1.alpha.,2.beta.,5.alpha.)]-: Human health tier I assessment

Chemie und Industrie

Verwendung und Herstellung

UsesPure form used only for scientific purposes; [OECD SIDS: IUCLID Data Set]
U.S. Production · 2 Einträge

2023: 1,000,000 - <5,000,000 lb

2023: 1,000,000 - <8,500,000 lb

Consumer UsesFragrance
Industry Uses · 2 Einträge

Odor agents

Odor agents

Household Products · 2 Einträge

Cosmetics product ingredient: Menthol (dl-menthol; l-menthol; d-menthol)

Information on 35 consumer products that contain Menthol (Racementhol) in the following categories is provided:

Use Classification · 2 Einträge

Fragrance Ingredients

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information · 4 Einträge

All Other Basic Organic Chemical Manufacturing

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel-: ACTIVE

Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)-: ACTIVE

Anwendungen · 2 Einträge

Beschreibung(+)-Menthol is a monoterpene alcohol that has been found in Cannabis and has antifungal activity. It inhibits the growth of F. verticillioides (MIC = 1.5 mM). Unlike (–)-menthol, (+)-menthol does not exhibit analgesia, antibacterial, anticancer, or cholinesterase inhibitory activities.

Verwenden(+)-MENTHOL is used for oral gel patch or film containing herb extracts or Chinese medicine, fruit extract, spearmint, and menthol for smoking cessation.

Zugehörige Reaktionen

6
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 1194901
HRID 1194901als Eduktuspto-grants-1989_03
Reaktionsgleichung von HRID 1245281
HRID 1245281als Eduktuspto-grants-2006_10
Reaktionsgleichung von HRID 1439226
HRID 1439226als Eduktuspto-grants-1977_11
Reaktionsgleichung von HRID 1741801
HRID 1741801als Eduktuspto-grants-1994_08
Reaktionsgleichung von HRID 2086540
HRID 2086540als Eduktuspto-grants-2004_04
Reaktionsgleichung von HRID 2414187
HRID 2414187als Produktals Eduktuspto-grants-1988_01

Notizen zur Verbindung

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421 °F at 760 mmHg (NTP, 1992)

212 °C ((-)-isomer 216.5)

Melting Point100 °F (NTP, 1992)
Vapor Density5.4 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
Vapor Pressure · 2 Einträge

1 mmHg at 133 °F approximately (NTP, 1992)

0.8 [mmHg]

Physikochemische Eigenschaften

Schmelzpunkt
43 · 43-44 °C (lit.)
Siedepunkt
103 · 103-104 °C/9 mmHg (lit.)
Dichte
0.89 · 0.890
Dampfdruck
0.8 mm · 0.8 mm Hg ( 20 °C)
Brechungsindex
50 ° · 50 ° (C=10, EtOH)
Flammpunkt
196 °F · 196 °F
storage temp.
2 · 2-8°C
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
pka
15.3 · 15.30±0.60(Predicted)
Farbe
Colourless to Off-White Oil
Geruch (Odor)
mentholic
Wasserlöslichkeit
Soluble in methanol (almost transparency), chloroform, alcohols, water (456 mg/L at 25°C), and ether.
BRN
1902292 · 1902292
Dielectric constant
3.2 · 3.2(Ambient)
InChI
1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m0/s1
InChIKey
NOOLISFMXDJSKH-AEJSXWLSSA-N
SMILES
CC(C)[C@H]1CC[C@H](C)C[C@@H]1O
LogP
3.15 at · 3.15 at 25℃
CAS Datenbank
15356 · 15356-60-2(CAS DataBase Reference)
EPA chemische Informationen
5 · Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)- (15356-60-2)
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Exposure may also cause hypersensitivity reactions including contact dermatitis, spasms of the glottis and collapse in young children, urticaria, flushing, headache, insomnia, unsteady gait, thick speech, tremor of the hands, mental confusion, depression, vomiting, cramp in the legs and bradycardia. Exposure to compounds of this class may cause painless blanching or erythema, possible corrosion, profuse sweating, intense thirst, nausea, diarrhea, cyanosis from methemoglobinemia, hyperactivity, stupor, blood pressure fall, hyperpnea, abdominal pain, hemolysis, convulsions, coma and pulmonary edema followed by pneumonia. If death from respiratory failure is not immediate, jaundice and oliguria or anuria may occur. These compounds occasionally cause skin sensitization.

Hazards Summary · 1 Eintrag

Menthol isomers demonstrate moderate skin and mild eye irritation; Low potential for skin sensitization; Low order of toxicity in repeated-dose oral studies (no specific systemic effects); No evidence of toxicity to fertility or development, teratogenicity, or carcinogenicity; [OECD SIDS] An irritant that may cause serious eye injury; [Sigma-Aldrich MSDS] See Menthol.

Reactive GroupAlcohols and Polyols
Reactivity Profile · 1 Eintrag

D,L-MENTHOL is incompatible with butyl chloral hydrate, camphor, phenol, chloral hydrate, Exalgine, betanaphthol, resorcinol or thymol in triturations; potassium permanganate, chromium trioxide and pyrogallol. It is also incompatible with strong oxidizers. (NTP, 1992)

Air and Water ReactionsInsoluble in water.
Hazard Classes and Categories · 2 Einträge

Skin Irrit. 2 (> 99.9%)

Acute Tox. 4 (10.9%)

Sicherheit und Schutzausrüstung

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

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 Eintrag

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 Eintrag

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)

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29061100
RTECS-Nr.
OT0700000
risk_code
37/38-41
hazard_code
Xi
safety_code
26-39
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Eye Dam. 1Skin Irrit. 2STOT SE 3

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Ethyl (R)-2-hydroxy-4-phenylbutyrateCyclohexane, 2-(ethenyloxy)-4-methyl-1-(1-methylethyl)-, (1R,2S,4S)-MONO-(1S)-(+)-MENTHYL PHTHALATE