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Merck
CN

59770

(−)-Isopulegol

analytical standard

Synonym(s):

(1R,2S,5R)-2-Isopropenyl-5-methylcyclohexanol, (1R,3R,4S)-p-Menth-8-en-3-ol

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About This Item

Empirical Formula (Hill Notation):
C10H18O
CAS Number:
89-79-2
Molecular Weight:
154.25
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329758715
EC Number:
201-940-6
Beilstein/REAXYS Number:
1906573
MDL number:
MFCD00134655

Key Documents

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Product Name

(−)-Isopulegol, analytical standard

InChI key

ZYTMANIQRDEHIO-KXUCPTDWSA-N

InChI

1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1

SMILES string

C[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C

grade

analytical standard

assay

≥99.0% (sum of enantiomers, GC)

optical activity

[α]20/D −22±0.5°, neat

optical purity

enantiomeric ratio: ≥99.5:0.5 (GC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

refractive index

n20/D 1.471 (lit.)
n20/D 1.472

bp

212 °C (lit.)

density

0.912 g/mL at 25 °C (lit.)

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

format

neat

Quality Level

100

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Application

(−)-Isopulegol may be used as an analytical reference standard for the determination of (−)-isopulegol in:
  • Complex commercial sample matrices by gas chromatography coupled to vacuum ultraviolet detector (GC-VUV).
  • Mentha piperita and M. arvensis essential oils by enantioselective GC.
  • Urine samples by high performance liquid chromatography combined with tandem mass spectrometry (HPLC-MS/MS).

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

General description

(−)-Isopulegol belongs to the class of terpene compounds occuring in various plant species.

Other Notes

Monoterpenoid chiral building block, hydroboration to a 1,4-diol
This compound is commonly found in plants of the genus: mentha

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

172.4 °F - closed cup

flash_point_c

78 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL4202
BCCJ9812
BCCH6013
BCCD1028
BCCB1587

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Enantioselective gas chromatography in flavor and fragrance analysis: strategies for the identification of known and unknown plant volatiles.
Konig WA and Hochmuth DH
Journal of Chromatographic Science, 42(8), 423-439 (2004)
G. Schmid et al.
Journal of the American Chemical Society, 105, 624-624 (1983)
Analysis of terpenes and turpentines using gas chromatography with vacuum ultraviolet detection.
Qiu C, et al.
Journal of Separation Science, 40(4), 869-877 (2017)
C.W. Jefford et al.
Organic Syntheses, 71, 207-207 (1993)
[The metabolic products of microorganisms. Boromycin].
R Hütter et al.
Helvetica chimica acta, 50(6), 1533-1539 (1967-01-01)
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