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62122

Sigma-Aldrich

(R)-(+)-Limonene

greener alternative

technical, ~90% (sum of enantiomers, GC)

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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:
12352002
PubChem Substance ID:
329759709
NACRES:
NA.22

vapor density

4.7 (vs air)

Quality Level

100

vapor pressure

<3 mmHg ( 14.4 °C)

grade

technical

Assay

~90% (sum of enantiomers, GC)

form

liquid

optical activity

[α]20/D +112±5°, c = 10% in ethanol

expl. lim.

6.1 %

greener alternative product characteristics

Waste Prevention
Safer Solvents and Auxiliaries
Use of Renewable Feedstocks
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sustainability

Greener Alternative Product

refractive index

n20/D 1.473 (lit.)

bp

176-177 °C (lit.)

solubility

water: insoluble

density

0.842 g/mL at 20 °C (lit.)

greener alternative category

Aligned,

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 an optically active (R) form of limonene. Limonene is a 10-carbon cyclohexanoid monoterpene. It is widely employed in cosmetic industry.
(R)-(+)-Limonene is present in the peel oil from citrus fruits. It is the most commonly used fragrance materials in technical products and in fine fragrances. It is the major constituent of the essential oil extracted from Anethum sowa Roxb. (Indian dill). Racemic limonene undergoes enantio-selective and enantio-specific conversion to (R)-(+)-α-terpineol byPenicillium digitatum mycelia. Biotransformation of (R)-(+)- and (S)-(-)-limonene by fungi has been investigated.

Application

(R)-(+)-Limonene has been used to investigate the in vitro and in vivo action of limonene against Leishmania species.

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)

123.8 °F

Flash Point(C)

51 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Bioconversion of (R)-(+)-limonene by P. digitatum (NRRL 1202)
Tan Q, et al.
Process. Biochem., 33(1), 29-37 (1998)
J C Demyttenaere et al.
Phytochemistry, 57(2), 199-208 (2001-05-31)
The biotransformation of (R)-(-)- and (S)-(-)-limonene by fungi was investigated. More than 60 fungal cultures were screened for their ability to bioconvert the substrate, using solid phase microextraction as the monitoring technique. After screening, the best fungal strains were selected
Antimicrobial activity profiles of the two enantiomers of limonene and carvone isolated from the oils of Mentha spicata and Anethum sowa.
Aggarwal KK, et al.
Flavour and Fragrance Journal, 17(1), 59-63 (2002)
Denise C Arruda et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 63(9), 643-649 (2009-03-27)
Limonene is a monoterpene that has antitumoral, antibiotic and antiprotozoal activity. In this study we demonstrate the activity of limonene against Leishmania species in vitro and in vivo. Limonene killed Leishmania amazonensis promastigotes and amastigotes with 50% inhibitory concentrations of
Cedric S Graebin et al.
European journal of medicinal chemistry, 45(4), 1524-1528 (2010-02-02)
The synthesis and in vitro activity of R(+)-Limonene derivatives against Leishmania and Trypanosoma cruzi strains are reported. Seven compounds have shown better in vitro activity against Leishmania (V.)braziliensis than the standard drug pentamidine. Additionally, we have identified two promising new
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