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H3916

Sigma-Aldrich

Hederagenin

≥97% (HPLC)

Synonym(s):

3,23-Dihydroxyolean-12-en-28-acid, Astrantiagenin E, Caulosapogenin, Hederagenic acid, Hederagenol

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About This Item

Empirical Formula (Hill Notation):
C30H48O4
CAS Number:
465-99-6
Molecular Weight:
472.70
MDL number:
MFCD00017385
UNSPSC Code:
41116107
NACRES:
NA.25

Assay

≥97% (HPLC)

solubility

methanol: 1 mg/mL

storage temp.

2-8°C

SMILES string

O[C@H]1CC[C@@]2(C)[C@](CC[C@]3(C)[C@]2([H])CC=C4[C@@]3(C)CC[C@]5(C(O)=O)[C@@]4([H])CC(C)(C)CC5)([H])[C@]1(C)CO

InChI

1S/C30H48O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1

InChI key

PGOYMURMZNDHNS-MYPRUECHSA-N

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Application

Hederagenin (3,23-Dihydroxyolean-12-en-28-acid), a triterpenoid saponin, is used to study the properties of triterpenoid saponins as biopesticides that prevent fungal growth, bacterial growth, and viral plant diseases. Hederagenin may be used as a reference in assays to detect it in biological fluids.

Biochem/physiol Actions

Saponin. Anti-inflammatory.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX2673
MKCL8266
MKCJ7336
MKCG6606
MKBZ9682V

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Oleanolic acid United States Pharmacopeia (USP) Reference Standard

USP

1478141

Oleanolic acid

Hederacoside C primary reference standard

00930585

Hederacoside C

β-Amyrin analytical standard

Supelco

09236

β-Amyrin

Jyoti Kalola et al.
Journal of AOAC International, 91(5), 1174-1178 (2008-11-05)
Fruit pericarp of Sapindus species are reported to contain glycosides with hederagenin as an aglycone. To free the aglycone from the glycosides, they need to be hydrolyzed, and the commonly used method is hydrolysis with either hydrochloric or sulfuric acid.
L Jayasinghe et al.
Phytochemistry, 40(3), 891-897 (1995-10-01)
Seven new saponins, all glycosides of hederagenin (3 beta,23- dihydroxyolean-12-en-28-oic acid), were isolated from the stem of Pometia eximia along with hederagenin and two known saponins. Their structures were established as 28-O-beta-D-apiosyl(1-->2)-beta-D-glucopyranosyl-, 3-O-alpha-L- arabinofuranosyl(1-->3)[alpha-L-rhamnopyranosyl (1-->2)]-beta-D- xylopyranosyl-, 3-O-beta-D-apiosyl(1-->3)[alpha-L-rhamnopyranosyl-(1-->2)-beta-D- glucopyranosyl-, 3-O-alpha-L-arabinofuranosyl(1-->3)[alpha-L-rhamnopyranosyl- (1-->2)]-beta-L-arabinopyranosyl-
Anti-inflammatory activities of hederagenin and crude saponin isolated from Sapindus mukorossi Gaertn.
K Takagi et al.
Chemical & pharmaceutical bulletin, 28(4), 1183-1188 (1980-01-01)
Nazlı Böke Sarıkahya et al.
Planta medica, 78(8), 828-833 (2012-04-13)
A phytochemical investigation of the aerial parts of Cephalaria elmaliensis resulted in the isolation of ten hederagenin-type triterpene saponins (1-10) including three new ones, elmalienoside A (1), elmalienoside B (2), elmalienoside C (3), and two known flavonoid glycosides (11-12). Their
Chen-Chen Zhu et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 47(1), 77-83 (2012-04-12)
A new triterpenoid saponin and fourteen known triterpenoids were isolated from the methanol extract of the stems and leaves of Callicarpa integerrima Champ, which is used in Chinese folk medicine for stopping bleeding, expelling the wind, dissipating stagnation, and treating
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