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W504505

Sigma-Aldrich

(S)-(−)-Limonene

≥95%, FG

Sinónimos:

(−)-p-Mentha-1,8-diene, (−)-Carvene, (S)-4-Isopropenyl-1-methyl cyclohexene

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About This Item

Fórmula empírica (notación de Hill):
C10H16
Número de CAS:
5989-54-8
Peso molecular:
136.23
Beilstein:
2323991
Número CE:
227-815-6
Número MDL:
MFCD00001558
Código UNSPSC:
12164502
ID de la sustancia en PubChem:
24902017
Número Flavis:
1.046
NACRES:
NA.21

origen biológico

synthetic

Nivel de calidad

400

grado

FG
Kosher

cumplimiento norm.

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

densidad de vapor

4.7 (vs air)

presión de vapor

<3 mmHg ( 14.4 °C)
1 mmHg ( 20 °C)

Ensayo

≥95%

actividad óptica

[α]20/D −90 to -61°, neat (angular)

lim. expl.

6.1 %

índice de refracción

n20/D 1.471 (lit.)

bp

175-177 °C (lit.)

densidad

0.844 g/mL at 25 °C (lit.)

aplicaciones

flavors and fragrances

Documentación

see Safety & Documentation for available documents

alérgeno alimentario

no known allergens

Organoléptico

camphoraceous; herbaceous; pine

cadena SMILES

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

Clave InChI

XMGQYMWWDOXHJM-SNVBAGLBSA-N

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Descripción general

(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.

Aplicación


  • 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).

Aplicación

Referencia del producto
Descripción
Precios

Palabra de señalización

Danger

Frases de peligro

H226,H304,H315,H317,H410

Clasificaciones de peligro

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

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

123.8 °F - closed cup

Punto de inflamabilidad (°C)

51 °C - closed cup

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
SHBN4496
SHBL4504
MKCJ3477
MKCF8370
MKCF2003

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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)
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
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
A Falk et al.
British journal of industrial medicine, 47(1), 62-64 (1990-01-01)
The liquid/air partition coefficients of four common terpenes, alpha-pinene, beta-pinene, 3-carene, and limonene, have been determined in vitro using head space technique. The liquids used were water, human blood, and olive oil. alpha-Pinene, beta-pinene, and 3-carene were practically insoluble in
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