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(R)-(+)-Limonene

analytical standard

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Synonym(s):
(+)-p-Mentha-1,8-diene, (+)-Carvene, (R)-4-Isopropenyl-1-methyl-1-cyclohexene
Empirical Formula (Hill Notation):
C10H16
CAS Number:
5989-27-5
Molecular Weight:
136.23
Beilstein:
2204754
EC Number:
227-813-5
MDL number:
MFCD00062991
UNSPSC Code:
85151701
PubChem Substance ID:
329759707
NACRES:
NA.24

grade

analytical standard

Quality Level

100

vapor density

4.7 (vs air)

vapor pressure

<3 mmHg ( 14.4 °C)

Assay

≥99.0% (sum of enantiomers, GC)

optical activity

[α]20/D +115.5±1°, c = 10% in ethanol

shelf life

limited shelf life, expiry date on the label

expl. lim.

6.1 %

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

refractive index

n20/D 1.473 (lit.)
n20/D 1.473

bp

176-177 °C (lit.)

density

0.842 g/mL at 20 °C (lit.)

application(s)

agriculture
cleaning products
cosmetics
environmental
flavors and fragrances
food and beverages
personal care

format

neat

storage temp.

2-8°C

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-/m0/s1

InChI key

XMGQYMWWDOXHJM-JTQLQIEISA-N

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General description

(R)-(+)-Limonene is the R- and the predominant enantiomer of the cyclic monoterpene, limonene. It is present as the major constituent of essential oils extracted from oranges, grapefruits, and lemons. In addition, it is also added as a flavoring agent in different personal and household cleaning products, beverages, and confectionery goods. It is known to possess antioxidant, antimicrobial, antifungal, anti-inflammatory, and anti-carcinogenic properties.

Application

This analytical standard can also be used as follows:
  • Analysis of alcoholic beverages for the determination of (R)-(+)-limonene by differential pulse voltammetry (DPV) using two novel electrochemical sensors
  • Simultaneous determination of limonene and linalool in 10 perfume product samples by two-dimensional high-performance liquid chromatographic (HPLC) method combined with electrospray ionization tandem mass spectrometry (ESI-MS/MS)
  • Determination of the enantiomeric composition of volatile chiral compounds, commonly present in three plant species from the Citrus genus by multidimensional gas chromatography (MDGC) coupled to mass spectrometry (MS)
  • Multi-residue analysis of volatiles and fatty acids found in wild and cultivated fennel samples by a single extraction method and gas chromatographic-flame ionization detection (GC-FID)

Other Notes

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Regioselective hydrogenation of the exocyclic double bond; Regioselective epoxidation of the endocyclic double bond

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. 1

WGK

WGK 2

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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R. Baker et al.
Journal of the Chemical Society. Chemical Communications, 414-414 (1987)
Whitefly attraction to rosemary (Rosmarinus officinialis L.) is associated with volatile composition and quantity
Sadeh D, et al.
PLoS ONE, 12(5) (2017)
Giuseppe Ferrandino et al.
Clinical and translational gastroenterology, 11(9), e00239-e00239 (2020-10-24)
Liver cirrhosis and its complication - hepatocellular carcinoma (HCC) - have been associated with increased exhaled limonene. It is currently unclear whether this increase is more strongly associated with the presence of HCC or with the severity of liver dysfunction.
T. Kitahara et al.
Tetrahedron, 43, 2689-2689 (1987)
Curtis A Gray et al.
PloS one, 10(9), e0135752-e0135752 (2015-09-04)
The tree-killing mountain pine beetle (Dendroctonus ponderosae Hopkins) is an important disturbance agent of western North American forests and recent outbreaks have affected tens of millions of hectares of trees. Most western North American pines (Pinus spp.) are hosts and
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Protocols

GC Analysis of Sweet Orange Essential Oil on SLB®-5ms (10 m x 0.10 mm I.D., 0.10 µm), Fast GC Analysis

-β-Farnesene; α-Huµlene; Germacrene D; (+)-Valencene; Bicyclogermacrene; (+)-δ-Cadinene

Related Content

Gas Chromatography (GC)

Gas chromatography separates volatile compounds in the gas phase, applied in various industries for quality control.

Chromatograms

suitable for GC

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