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10,11-Dihydroxy-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

HCID 5320146
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Basic information

CAS
465-00-9
Standard SMILES
CC1(C)CCC2(C(=O)O)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5CCC43C)C2C1
InChIKey
RWNHLTKFBKYDOJ-UHFFFAOYSA-N
Molecular formula
C30H48O5
Average molar mass
488.7 g/mol
Monoisotopic mass
488.35017463

Overview

10,11-Dihydroxy-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 is a triterpenoid.

Names & identifiers

Preferred name
10,11-Dihydroxy-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
IUPAC
10,11-dihydroxy-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
Arjunolic acid
Molecular formula
C30H48O5
Molecular weight
488.7

Names & synonyms

10,11-dihydroxy-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 acidBayogenin [M+H]+Compound NP-016593MLS004491897CHEBI:181177AGA82116CEA51934AKOS040738589SMR003288841B2703-092741Olean-12-en-28-oicacid, 2,3,23-trihydroxy-, (2a,3a,4b)-arjunolicaci
Show more names
Arjulic acidarjunolic acidArjunolic acid, 10 mM in DMSOArjunolic acid >=95% (LC/MS-ELSD)2,3,23-Trihydroxyolean-12-en-28-oic acidOlean-12-en-28-oicacid, 2,3,23-trihydroxy-, (2a,3b,4a)-(2alpha,3beta,4alpha)-2,3,23-Trihydroxy-olean-12-en-28-oic acidhepatocyte injury,hyperglycemia,Inhibitor,type 1 diabetes,antimicrobial,antioxidant,Reactive Oxygen Species,Antidiabetic,Arjunolic acid,antibacterial,inhibit,Symplocos lancifolia,reactive oxygen(4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-10,11-Dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid

Database identifiers

CAS
465-00-9
PubChem CID
5320146
ChEBI
CHEBI:181177

Properties

Computed structural properties

XLogP
5.8
Topological polar surface area
98 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
5
Rotatable bonds
2
Heavy atoms
35
Formal charge
0
Complexity
941

Experimental & physicochemical properties

Melting Point337 - 340 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
332 · 332-334 °C
Boiling point
606 · 606.0±55.0 °C(Predicted)
Density
1.19 · 1.19±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
solubility
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form
Powder
pka
4.62 · 4.62±0.70(Predicted)
color
White to off-white
Major Application
metabolomicsvitamins, nutraceuticals, and natural products
InChIKey
RWNHLTKFBKYDOJ-QBUVGUFVNA-N
SMILES
[C@@H]1(O)C[C@@]2([C@@]3([H])CC=C4[C@]5([C@](C(O)=O)(CCC(C)(C)C5)CC[C@@]4(C)[C@]3(C)CC[C@@]2([H])[C@](C)(CO)[C@H]1O)[H])C |&1:0,3,4,9,10,22,24,28,30,34,r|
UNSPSC Code
12352205 · 12352205
NACRES
25 · NA.25
WGK Germany
3 · 3
Storage Class
11 · 11 - Combustible Solids

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
3
Storage Class
11 - Combustible Solids

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular
Applications · 2 items

DescriptionArjunolic acid is a triterpene that has been found in T. arjuna and has diverse biological activities, including antioxidant, anticancer, and anti-inflammatory properties. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell-free assay when used at a concentration of 0.8 mM. Arjunolic acid (20 mg/kg for four days) prevents arsenic-induced decreases in the activity of superoxide dismutase (SOD1), catalase, GST, and glutathione reductase in mouse brain. It reduces tumor growth in an Ehrlich murine spontaneous adenocarcinoma model when administered at doses of 100 and 250 mg/kg for 20 days. Arjunolic acid reduces renal fibrosis and increases in kidney TNF-α and IL-1β levels induced by cisplatin in mice when administered at doses of 100 and 250 mg/kg per day for 10 days.

UsesArjunolic Acid is a naturally occurring terpenoid which displays anti-inflammatory activity as well as protective effects during chemical induced organ pathophysiology.

Additional notes · 1 item

DefinitionChEBI: A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensi , it exhibits antioxidant and antimicrobial activities.

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