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218367

Sigma-Aldrich

(S)-(−)-Limonene

96%

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:
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

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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 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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ6807
MKCN5717
MKCK9299
MKCJ9898
MKCH7457

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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
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