D-Menthol

MENTHOL Struktur
15356-70-4
CAS-Nr.
15356-70-4
Bezeichnung:
D-Menthol
Englisch Name:
MENTHOL
Synonyma:
D-Menthol;Menthol racemic;2-Isopropyl-5-methylcyclohexanol;racementhol;FEMA 2665;MENTHOL;NCI-C50000;3-p-Menthol;d,1-menthol;MENTHOL, DL-
CBNumber:
CB7116412
Summenformel:
C10H20O
Molgewicht:
156.27
MOL-Datei:
15356-70-4.mol

D-Menthol Eigenschaften

Schmelzpunkt:
34-36 °C(lit.)
Siedepunkt:
216 °C(lit.)
Dichte
0.89 g/mL at 25 °C(lit.)
Dampfdruck
0.8 mm Hg ( 20 °C)
FEMA 
2665 | MENTHOL RACEMIC
Brechungsindex
1.4615
Flammpunkt:
200 °F
storage temp. 
2-8°C
Löslichkeit
Practically insoluble in water, very soluble in ethanol (96 per cent) and in light petroleum, freely soluble in fatty oils and in liquid paraffin, very slightly soluble in glycerol.
Aggregatzustand
cryst.
Farbe
White
Dielectric constant
3.2(Ambient)
InChIKey
NOOLISFMXDJSKH-UHFFFAOYSA-N
CAS Datenbank
15356-70-4(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,Xi
R-Sätze: 37/38-41-48/20/22-40-38-22
S-Sätze: 36/37/39-36-26
RIDADR  UN 1888 6.1/PG 3
WGK Germany  2
RTECS-Nr. OT0525000
HS Code  29061100
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung P264, P270, P301+P312, P330, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
H331 Giftig bei Einatmen. Akute Toxizität inhalativ Kategorie 3 Achtung P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H336 Kann Schläfrigkeit und Benommenheit verursachen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Schläfrigkeit und Benommenheit) Warnung P261, P271, P304+P340, P312,P403+P233, P405, P501
H351 Kann vermutlich Krebs verursachen. Karzinogenität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
H372 Schädigt bei Hautkontakt und Verschlucken die Organe bei längerer oder wiederholter Exposition. Spezifische Zielorgan-Toxizität (wiederholte Exposition) Kategorie 1 Achtung P260, P264, P270, P314, P501
Sicherheit
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P301+P312 BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P302+P352 BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
P308+P313 BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

D-Menthol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R37/38:Reizt die Atmungsorgane und die Haut.
R41:Gefahr ernster Augenschäden.
R48/20/22:Gesundheitsschädlich: Gefahr ernster Gesundheitsschäden bei längerer Exposition durch Einatmen und durch Verschlucken.
R40:Verdacht auf krebserzeugende Wirkung.
R38:Reizt die Haut.
R22:Gesundheitsschädlich beim Verschlucken.

S-Sätze Betriebsanweisung:

S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.

Chemische Eigenschaften

Racemic menthol is a mixture of equal parts of the (1R,2S,5R)- and (1S,2R,5S)-isomers of menthol. It is a free-flowing or agglomerated crystalline powder, or colorless, prismatic, or acicular shiny crystals, or hexagonal or fused masses with a strong characteristic odor and taste. The crystalline form may change with time owing to sublimation within a closed vessel. The USP 32 specifies that menthol may be either naturally occurring l-menthol or syntheti-cally prepared racemic or dl-menthol. However, the JP XV and PhEur 6.0, along with other pharmacopeias, include two separate monographs for racemic and l-menthol.

Physikalische Eigenschaften

Physical Properties. The eight optically active menthols differ in their sensory properties. (?)-Menthol has a characteristic peppermint odor and also exerts a cooling effect. The other isomers do not possess this cooling effect and are, therefore, not considered to be “refreshing.” Racemic menthol occupies an intermediate position; the cooling effect of the (?)-menthol present is distinctly perceptible.
The enantiomeric menthols have identical physical properties (apart from their specific rotations), but the racemates differ from the optically active forms in, for example, theirmelting points.Although the differences between the boiling points are small, the (racemic) stereoisomers can be separated by fractional distillation. Boiling points (in °C at 101.3 kPa) are as follows:
rac-neomenthol, 211.7
rac-neoisomenthol 214.6
rac-menthol, 216.5
rac-isomenthol, 218.6
Other physical constants of commercially available levorotatory and racemic menthols are as follows: (?)-menthol, mp 43 °C, [α]20 D ?50° (ethanol, 10%); racemic menthol, mp 38 °C.
Chemical Properties. Hydrogenation of menthols yields p-menthane; oxidation with chromic acid or catalytic dehydrogenation yields menthones. Dehydration under mild conditions yields 3-p-menthene as the main product. Reaction with carboxylic acids or their derivatives yields menthyl esters, which are used mainly as aroma substances and in pharmaceutical preparations and formulations. The esterification of menthols with benzoic acid is used on an industrial scale in the resolution of racemic menthol.

Occurrence

Has apparently not been reported to occur in nature

synthetische

By hydrogenation of thymol followed by separation from its other isomers.

Indications

Menthol, a cyclic alcohol (derived from peppermint, other mint oils, or prepared synthetically), relieves itching by generating a cool sensation. It is usually used in 0.25% to 2% concentrations but is present in concentrations as high as 16% in some OTC products.

Vorbereitung Methode

Menthol occurs widely in nature as l-menthol and is the principal component of peppermint and cornmint oils obtained from the Mentha piperita and Mentha arvensis species. Commercially, lmenthol is mainly produced by extraction from these volatile oils. It may also be prepared by partial or total synthetic methods.
Racemic menthol is prepared synthetically via a number of routes, e.g. by hydrogenation of thymol.

Pharmazeutische Anwendungen

Menthol is widely used in pharmaceuticals, confectionery, and toiletry products as a flavoring agent or odor enhancer. In addition to its characteristic peppermint flavor, l-menthol, which occurs naturally, also exerts a cooling or refreshing sensation that is exploited in many topical preparations. Unlike mannitol, which exerts a similar effect due to a negative heat of solution, l-menthol interacts directly with the body’s coldness receptors. d-Menthol has no cooling effect, while racemic menthol exerts an effect approximately half that of l-menthol.
When used to flavor tablets, menthol is generally dissolved in ethanol (95%) and sprayed onto tablet granules and not used as a solid excipient.
Menthol has been investigated as a skin-penetration enhancer and is also used in perfumery, tobacco products, chewing gum and as a therapeutic agent. When applied to the skin, menthol dilates the blood vessels, causing a sensation of coldness followed by an analgesic effect. It relieves itching and is used in creams, lotions, and ointments. When administered orally in small doses menthol has a carminative action.

Sicherheitsprofil

Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An eye and skin irritant. K%en heated to decomposition it emits acrid smoke and irritating fumes. See also MENTHOL and 1-MENTHOL.

Sicherheit(Safety)

Almost all toxicological data for menthol relate to its use as a therapeutic agent rather than as an excipient. Inhalation or ingestion of large quantities can result in serious adverse reactions such as ataxia and CNS depression,hypersensitivity reactions, severe abdominal pain, nausea, vomiting, vertigo, drowsiness, and coma.Although menthol is essentially nonirritant there have been some reports of hypersensitivity following topical application. In a Polish study approximately 1% of individuals were determined as being sensitive to menthol.There have been reports of apnea and instant collapse in infants after the local application of menthol to their nostrils.
The WHO has set an acceptable daily intake of menthol at up to 0.4 mg/kg body-weight.
LD50 (rat, IM): 10.0 g/kg
LD50 (rat, oral): 3.18 g/kg

Stoffwechsel

Rabbits are said to eliminate 59% of dl-menthol as glucuronide (Williams, 1938).

Lager

A formulation containing menthol 1% w/w in aqueous cream has been reported to be stable for up to 18 months when stored at room temperature.
Menthol should be stored in a well-closed container at a temperature not exceeding 25°C, since it sublimes readily.

Inkompatibilitäten

Incompatible with: butylchloral hydrate; camphor; chloral hydrate; chromium trioxide; b-naphthol; phenol; potassium permanganate; pyrogallol; resorcinol; and thymol.

Regulatory Status

Included in the FDA Inactive Ingredients Database (dental preparations, inhalations, oral aerosols, capsules, solutions, suspensions, syrups, and tablets; also topical preparations). Included in nonparenteral medicines licensed in the UK. Accepted for use in foods and confectionery as a flavoring agent of natural origin. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

D-Menthol Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


D-Menthol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 219)Lieferanten
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career henan chemical co
+86-0371-86658258
sales@coreychem.com China 29914 58
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18871490254
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+86-023-61398051 +8613650506873
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15356-70-4(D-Menthol)Verwandte Suche:


  • 3-p-Menthol
  • 4-Isopropyl-1-methylcyclohexan-3-ol
  • mentholracemique
  • NCI-C50000
  • MENTHOL, DL-
  • (+/-)-MENTHOL
  • MENTHOL
  • HEXAHYDROTHYMOL 2-ISOPROPYL-5-METHYLCYCLOHEXANOL
  • DL-MENTHAN-3-OL
  • DL-4-MENTHAN-3-OL
  • DL-2-ISOPROPYL-5-METHYLCYCLOHEXANOL
  • 5-METHYL-2-(1-METHYETHYL)CYCLOHEXANOL
  • (1RS,3RS,4SR)-4 MENTHAN-3-OL
  • DL-Menthol, racemic
  • CYCLOHEXANOL,5-METHYL-2-(1-ME
  • Menthol solution
  • DL-MENTHOL USP (RACEMIC) SYNTHETIC
  • D,L-Menthol solution
  • mentholracemic
  • Menthol, cis-1,3,trans-1,4-(.+/-.)-
  • Menthol, cis-1,3,trans-1,4-(±
  • Menthol, (±
  • Menthol racemique
  • dl-3-p-Menthanol
  • d,1-menthol
  • cyclohexanol,5-methyl-2-(1-methylethyl)-,(1-alpha,2-beta,5-alpha)
  • Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1alpha,2beta,5alpha)-(±
  • cis-1,3-trans-1,4-(+-)-mentho
  • 5-methyl-2-(1-methylethyl)-,(1alpha,2beta,5alpha)-(+/-)-cyclohexano
  • 5-methyl-2-(1-methylethyl)-,(1.alpha.,2.beta.,5.alpha.)-(+-)-Cyclohexanol
  • (+/-)-p-Menthan-3-ol
  • Menthol cristal
  • racementhol
  • FEMA 2665
  • 2-Isopropyl-5-methylcyclohexanol
  • D-Menthol
  • Menthol racemic
  • 15356-70-4
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