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SMB00177

Sigma-Aldrich

Kaurenoic acid

≥95% (LC/MS-ELSD)

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Synonym(s):
Ent-kaurenoic acid, Kaur-16-en-18-oic acid, Kauren-19-oic acid, Kaurenic acid, Cunabic acid
Empirical Formula (Hill Notation):
C20H30O2
CAS Number:
6730-83-2
Molecular Weight:
302.45
UNSPSC Code:
12352205
PubChem Substance ID:
329824843
NACRES:
NA.25

Quality Level

200

Assay

≥95% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

C=C1C[C@@]23CC[C@]4([H])[C@@](C(O)=O)(C)CCC[C@@]4(C)[C@]2([H])CC[C@@H]1C3

InChI

1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15+,16+,18-,19-,20-/m1/s1

InChI key

NIKHGUQULKYIGE-OTCXFQBHSA-N

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General description

Natural product derived from plant source.

Biochem/physiol Actions

Kaurenoic acid (KA) is a diterpene which displays selective antibacterial activity against Gram-positive bacteria. Kaurenoic acid exhibits uterine relaxant activity via calcium blockade and opening ATP-sensitive potassium channels.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Sho Miyazaki et al.
FEBS letters, 585(12), 1879-1883 (2011-05-07)
The moss Physcomitrella patens produces both ent-kaurene and ent-kaurenoic acid, which are intermediates of gibberellin biosynthesis in flowering plants. The CYP701 superfamily of cytochrome P450s functions as ent-kaurene oxidases in the biosynthesis of ent-kaurenoic acid. A candidate gene encoding ent-kaurene
Giovana Fucina et al.
Talanta, 101, 530-536 (2012-11-20)
A gradient stability indicative HPLC-UV method was developed and validated for assay of the marker kaurenoic acid (KA) in spray dried extract of Sphagneticola trilobata (L.) Pruski. The marker, and another unidentified polar component, were separated on a Luna Phenomenex
R Guillopé et al.
Phytotherapy research : PTR, 25(12), 1861-1864 (2011-04-27)
Guadeloupean Parkinsonism has been linked epidemiologically to the consumption of Annonaceae fruits. These were proposed to be etiological agents for sporadic atypical Parkinsonism worldwide, because of their content of neurotoxins such as isoquinolinic alkaloids and Annonaceous acetogenins. The pulp of
Xin-Xin Xie et al.
Chinese journal of natural medicines, 15(8), 625-630 (2017-09-25)
The kaurenoic acid-type diterpenoids in Acanthopanacis Cortex have been reported to be the major active components. However, the diterpenoids are present as position isomers that exacerbate the challenges in obtaining standards compounds. Little work has been done on the quantitative
Simone Ribeiro Lucho et al.
Physiology and molecular biology of plants : an international journal of functional plant biology, 24(5), 767-779 (2018-08-29)
Stevia rebaudiana is an important source of natural steviol glycosides and is of increasing interest in various fields of study. Therefore, understanding the molecular processes regulating its metabolism is of great importance. In this study, the stability of seven reference
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