Skip to Content
Merck
All Photos(3)

Documents

218367

Sigma-Aldrich

(S)-(−)-Limonene

96%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

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:
12352002
PubChem Substance ID:
24853063
NACRES:
NA.22

vapor density

4.7 (vs air)

Quality Level

100

vapor pressure

<3 mmHg ( 14.4 °C)
1 mmHg ( 20 °C)

Assay

96%

form

liquid

optical activity

[α]19/D −94°, c = 10 in ethanol

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.)

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

(S)-(-)-Limonene, a monoterpenoid compound, is mostly used in perfumery and in flavoring. On irradiation, it undergoes radiolysis, which leads to a reduction in the optical purity. (S)-(-)-Limonene also shows potent antimicrobial activity.

Signal Word

Danger

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 6

1 of 6

(R)-(+)-Limonene primary reference standard

00590590

(R)-(+)-Limonene

(1S,2R,5S)-(+)-Menthol 99%

Sigma-Aldrich

224464

(1S,2R,5S)-(+)-Menthol

(1R,2S,5R)-(&#8722;)-Menthol ReagentPlus&#174;, 99%

Sigma-Aldrich

M2780

(1R,2S,5R)-(−)-Menthol

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

Supelco

CRM40448

Limonene solution

(S)-(+)-Carvone for synthesis

Sigma-Aldrich

8.18410

(S)-(+)-Carvone

(&#8722;)-&#945;-Pinene 98%, optical purity ee: &#8805;81% (GLC)

Sigma-Aldrich

P45702

(−)-α-Pinene

Antimicrobial activity of limonene enantiomers and 1, 8-cineole alone and in combination.
Van Vuuren SF and Viljoen AM.
Flavour and Fragrance Journal, 22(6), 540-544 (2007)
Malaria parasites produce volatile mosquito attractants.
Kelly M, et al.
mBio, 6(2), e00235-e00215 (2015)
Gamma-radiolysis of chiral molecules: R (+)-limonene, S (-)-limonene and R (-)-a-phellandrene.
Cataldo F, et al.
J. Radioanal. Nucl. Chem., 262(2), 423-428 (2004)
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service