Basic information
- CAS
465-99-6- Standard SMILES
CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]2C1- InChIKey
PGOYMURMZNDHNS-MYPRUECHSA-N- Molecular formula
- C30H48O4
- Average molar mass
- 472.7 g/mol
- Monoisotopic mass
- 472.35526001
Overview
Hederagenin is a sapogenin that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 3 and 23 (the 3beta stereoisomer). It has a role as a plant metabolite. It is a pentacyclic triterpenoid, a sapogenin and a dihydroxy monocarboxylic acid. It is functionally related to an oleanolic acid. It is a conjugate acid of a hederagenin(1-). It derives from a hydride of an oleanane.
Names & identifiers
- Preferred name
- Hederagenin
- IUPAC
- (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
- English name
- Hederagenin
- Molecular formula
- C30H48O4
- Molecular weight
- 472.71
Names & synonyms
Hederagenin465-99-6CaulosapogeninHederagenolAstrantiagenin EHederagenic acid(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acidCyclocaric acid ANSC-24954(3beta)-3,23-dihydroxyolean-12-en-28-oic acidRQF57J8212(3-beta,4-alpha)-3,23-Dihydroxyolean-12-en-28-oic acid
Show more names
HederidinNSC 24954HederogeninRangefinderHederagenineMELANTHIGENINVaccaric acidKalosapogenin
CHEBI:69579Olean-12-en-28-oic acid, 3,23-dihydroxy-, (3beta,4alpha)-DTXSID301029412RefChem:38603DTXCID501514667207-369-9HerderageninOlean-12-en-28-oic acid, 3,23-dihydroxy-, (3b,4a)-
Database identifiers
Properties
Computed structural properties
- XLogP
- 6.8
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 907
Experimental & physicochemical properties
Collision Cross Section
210.6 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
209.73 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 332 · 332-334°
- alpha
- 20 · D20 +81° (c = 0.7 in pyridine)
- Boiling point
- 493.44 °C · 493.44°C (rough estimate)
- Density
- 0.9871 · 0.9871 (rough estimate)
- refractive index
- 1.48 · 1.4800 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 1 mg/mL · methanol: soluble1mg/mL
- pka
- 4.63 · 4.63±0.70(Predicted)
- form
- Solid
- color
- White to Off-White
- λmax
- 405 nm · 405nm(H2SO4)(lit.)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports.
Warning
H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (33.3%)
Safety data
- wgk
- 3
- hs_code
- 29181990
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 22-45-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312+P330-P501
Chemistry & industry
Applications
DescriptionHederagenin is a triterpene saponin that has been found in P. eximia with diverse biological activities. It increases production of reactive oxygen species (ROS), reduces colony formation, and induces apoptosis in cisplatin-resistant head and neck carcinoma (HNC) cells. In vivo, hederagenin (50, 100, and 200 mg/kg) suppresses tumor growth in a cisplatin-resistant HNC mouse xenograft model. It reduces aortic atherosclerotic lesion area, serum cholesterol and LDL levels, and inducible nitric oxide synthase (iNOS) protein levels in a rat model of atherosclerosis. Hederagenin (50 mg/kg) reduces ethanol-induced production of TNF-α, IL-6, and COX-2, alcohol dehydrogenase 2 (ALDH2) mRNA expression, and liver damage in a rat model of alcohol-induced hepatotoxicity. It also induces autophagy and inhibits oligomerization of α-synuclein in a mouse model of Parkinson''s disease induced by MPTP.
UsesTriterpenoid which can inhibit the proliferation of leukemia HL-60 cells.
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山西玉宁生物科技有限公司13623677056 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
陕西帕尼尔生物科技有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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