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Merck
CN

68612

Bakuchiol

analytical standard

Synonym(s):

(S)-Bakuchiol, 4-[(1E,3S)-3-Ethenyl-3,7-dimethyl-1,6-octadien-1-yl]phenol

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About This Item

Empirical Formula (Hill Notation):
C18H24O
CAS Number:
10309-37-2
Molecular Weight:
256.38
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329761022
MDL number:
MFCD01707441
Beilstein/REAXYS Number:
3611720

Key Documents

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InChI

1S/C18H24O/c1-5-18(4,13-6-7-15(2)3)14-12-16-8-10-17(19)11-9-16/h5,7-12,14,19H,1,6,13H2,2-4H3/b14-12+/t18-/m1/s1

SMILES string

C\C(C)=C/CC[C@@](C)(C=C)\C=C\c1ccc(O)cc1

InChI key

LFYJSSARVMHQJB-QIXNEVBVSA-N

grade

analytical standard

assay

≥95.0% (HPLC)

optical activity

[α]/D +24.0 to +30.0°, c = 0.1 in chloroform

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

food and beverages

format

neat

storage temp.

−20°C

Quality Level

100

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Application

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

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

363.2 °F - Pensky-Martens closed cup

flash_point_c

184 °C - Pensky-Martens closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD6908
BCCK7461
BCCG7662
BCCG0499
BCCB9679

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Osamu Ohno et al.
Bioscience, biotechnology, and biochemistry, 74(7), 1504-1506 (2010-07-14)
An EtOH extract of fruits of Piper longum was found to exhibit a potent inhibitory effect against alpha-melanocyte-stimulating hormone (alpha-MSH)-induced melanin production in B16 mouse melanoma cells. Bioassay-directed fractionation led to the isolation of prenylated phenolic compounds bakuchiol, bavachin, and
Kit-Man Lau et al.
The American journal of Chinese medicine, 38(5), 1005-1014 (2010-09-08)
Fructus Psoraleae and Folium Eucalypti Globuli have long been used as Chinese medicines to treat various ailments such as asthma, eczema and dermatomycosis. In previous studies, their antifungal activities were demonstrated. The aim of the present study was to isolate
Ken-ichi Takao et al.
Molecules (Basel, Switzerland), 17(11), 13330-13344 (2012-11-10)
An asymmetric Claisen rearrangement using Oppolzer’s camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from
Ai-fang Li et al.
Beijing da xue xue bao. Yi xue ban = Journal of Peking University. Health sciences, 44(3), 431-436 (2012-06-14)
To analyze cytochrome P450 (CYP) phenotyping for bakuchiol metabolism and study the mechanism of detoxification of bakuchiol by human liver microsomes (HLM) in vitro. The CYP phenotyping for bakuchiol metabolism was determined using HLM combined with CYP specific inhibitors and
Sang Yoon Choi et al.
Journal of medicinal food, 13(4), 1019-1023 (2010-06-18)
The bark of the root and stem of Ulmus davidiana var. japonica has been used as a traditional Korean medicine to treat inflammatory disorders. This plant reportedly exhibits antioxidant, anticancer, and anti-inflammatory effects. A search for biologically active compounds in
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