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62122

Sigma-Aldrich

(R)-(+)-Limonene

greener alternative

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

Synonyma:

(+)-p-Mentha-1,8-diene, (+)-Carvene, (R)-4-Isopropenyl-1-methyl-1-cyclohexene

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About This Item

Empirický vzorec (Hillův zápis):
C10H16
Číslo CAS:
5989-27-5
Molekulová hmotnost:
136.23
Beilstein/REAXYS Number:
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
Learn more about the Principles of Green Chemistry.

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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Související kategorie

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.

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Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

123.8 °F - closed cup

flash_point_c

51 °C - closed cup

ppe

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

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Osvědčení o analýze (COA)

Lot/Batch Number
BCCF2454
BCBZ1768
BCBR2678V
BCBM1151V
BCBH9990V

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Limonene solution certified reference material, 2000&#160;&#956;g/mL in methanol, ampule of 1&#160;mL

Supelco

CRM40448

Limonene solution

(+)-Limonene 1,2-epoxide mixture of cis/trans-isomers, &#8805;97.0% (sum of isomers, GC)

Sigma-Aldrich

17763

(+)-Limonene 1,2-epoxide

(R)-(&#8722;)-Carvone 98%

Sigma-Aldrich

124931

(R)-(−)-Carvone

3-Carene 90%

Sigma-Aldrich

115576

3-Carene

(S)-(+)-Carvone 96%

Sigma-Aldrich

435759

(S)-(+)-Carvone

Myrcene technical grade

Sigma-Aldrich

M100005

Myrcene

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)
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
Bioconversion of (R)-(+)-limonene by P. digitatum (NRRL 1202)
Tan Q, et al.
Process. Biochem., 33(1), 29-37 (1998)
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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Chromatograms

suitable for GC

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