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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

Quality Level

100

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)
Zhong-Yi Zhang et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 32(9), 786-788 (2007-07-21)
To compare the quality of Flos Lonicerae between different producing areas. ICP-AES, UV and HPLC were used to determine the contents of trace elements, chlorogenic acid, total flavonoids, five iridoid glucosides, hederagenin, and oleanolic acid. SAS software system was used
Qiongming Xu et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 34(20), 2610-2612 (2010-01-15)
To investigate the chemical constituents from roots of Boehmeria nivea. The constituents were isolated by repeated column chromatography and preparative liquid chromatography; and their structures were elucidated by chemical properties and spectroscopic analyses. Seven compounds were isolated and their structures
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