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W504505

Sigma-Aldrich

(S)-(−)-Limonene

≥95%, FG

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H16
CAS Number:
5989-54-8
Molecular Weight:
136.23
Beilstein:
2323991
EC Number:
227-815-6
MDL number:
MFCD00001558
UNSPSC Code:
12164502
PubChem Substance ID:
24902017
Flavis number:
1.046
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Kosher

reg. compliance

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

vapor density

4.7 (vs air)

vapor pressure

<3 mmHg ( 14.4 °C)
1 mmHg ( 20 °C)

Assay

≥95%

optical activity

[α]20/D −90 to -61°, neat (angular)

expl. lim.

6.1 %

refractive index

n20/D 1.471 (lit.)

bp

175-177 °C (lit.)

density

0.844 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

Organoleptic

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

InChI key

XMGQYMWWDOXHJM-SNVBAGLBSA-N

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General description

(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.

Application


  • 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).

Signal Word

Danger

Hazard Statements

H226,H304,H315,H317,H410

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

123.8 °F - closed cup

Flash Point(C)

51 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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 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
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.
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
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
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