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W504505

Sigma-Aldrich

(S)-(−)-Limonen

≥95%, FG

Synonym(e):

(−)-Carven, 4-Isopropenyl-1-methyl-1-cyclohexen, p-Mentha-1,8-dien

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About This Item

Empirische Formel (Hill-System):
C10H16
CAS-Nummer:
5989-54-8
Molekulargewicht:
136.23
Beilstein:
2323991
EG-Nummer:
227-815-6
MDL-Nummer:
MFCD00001558
UNSPSC-Code:
12164502
PubChem Substanz-ID:
24902017
Flavis-Nummer:
1.046
NACRES:
NA.21

Biologische Quelle

synthetic

Qualitätsniveau

400

Qualität

FG
Kosher

Einhaltung gesetzlicher Vorschriften

EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 182.60

Dampfdichte

4.7 (vs air)

Dampfdruck

<3 mmHg ( 14.4 °C)
1 mmHg ( 20 °C)

Assay

≥95%

Optische Aktivität

[α]20/D −90 to -61°, neat (angular)

Expl.-Gr.

6.1 %

Brechungsindex

n20/D 1.471 (lit.)

bp

175-177 °C (lit.)

Dichte

0.844 g/mL at 25 °C (lit.)

Anwendung(en)

flavors and fragrances

Dokumentation

see Safety & Documentation for available documents

Nahrungsmittelallergen

no known allergens

Organoleptisch

camphoraceous; herbaceous; pine

SMILES String

CC(=C)[C@H]1CCC(C)=CC1

InChI

1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m1/s1

InChIKey

XMGQYMWWDOXHJM-SNVBAGLBSA-N

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Verwandte Kategorien

Allgemeine Beschreibung

(S)-(−)-Limonene, a fragrance monoterpene, is mainly found in citrus peel oil. It is also found in the essential oils of herbs such as rosemary, eucalyptus, lavender, caraway, lemongrass, and peppermint) and also tea tree oil, and turpentine oil. The oxidation products of limonene may lead to fragrance-related contact allergy.

Anwendung


  • Efficient production of (S)-limonene and geraniol in Saccharomyces cerevisiae through the utilization of an Erg20 mutant with enhanced GPP accumulation capability.: This study highlights a metabolic engineering approach to enhance the production of (S)-limonene and geraniol in yeast, offering potential for scalable biosynthesis of these valuable compounds (Bernard et al., 2024).

  • The behavioral sensitivity of mice to acyclic, monocyclic, and bicyclic monoterpenes.: This research investigates the effects of various terpenes including (S)-limonene on mice behavior, providing insights into potential therapeutic applications (Williams et al., 2024).

Anwendung

Produkt-Nr.
Beschreibung
Preisangaben

Signalwort

Danger

Gefahreneinstufungen

Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1B

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 2

Flammpunkt (°F)

123.8 °F - closed cup

Flammpunkt (°C)

51 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Not only oxidized R?(+)?but also S?(?)?limonene is a common cause of contact allergy in dermatitis patients in Europe.
Matura M, et al.
Contact Dermatitis, 55(5), 274-279 (2006)
Perry Fung Chye Lim et al.
International journal of pharmaceutics, 311(1-2), 157-164 (2006-02-03)
Penetration enhancers are a classical means for improving transdermal drug delivery (TDD). Enhancers permeate into the skin and reversibly decrease the barrier resistance. Basically, our aim is to formulate a transdermal gel containing an appropriate enhancer for a controlled drug
G C Hard et al.
Critical reviews in toxicology, 24(3), 231-254 (1994-01-01)
The naturally occurring food constituent d-limonene has been found to cause tumors at high doses only in the kidney of the male rat in association with the development of hyaline droplet nephropathy. In contrast, neither kidney tumors nor the associated
P L Crowell et al.
Critical reviews in oncogenesis, 5(1), 1-22 (1994-01-01)
The naturally occurring monoterpene d-limonene has chemopreventive and chemotherapeutic activity against many rodent solid tumor types. The chemopreventive activity of limonene during initiation can be attributed to the induction of phase I and phase II enzymes, with resulting carcinogen detoxification.
P A Cornwell et al.
The Journal of pharmacy and pharmacology, 46(12), 938-950 (1994-12-01)
Wide-angle X-ray-diffraction experiments were used to investigate the molecular organization of barrier components of human stratum corneum. Diffraction lines related to the side-by-side lipid packing arrangements in the intercellular bilayers were identified as were patterns arising from secondary protein structures
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