Basic information
- CAS
465-00-9- Standard SMILES
CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]2C1- InChIKey
RWNHLTKFBKYDOJ-DDHMHSPCSA-N- Molecular formula
- C30H48O5
- Average molar mass
- 488.7 g/mol
- Monoisotopic mass
- 488.35017463
Overview
Arjunolic acid is 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 sinensis, it exhibits antioxidant and antimicrobial activities. It has a role as an antioxidant, a metabolite, an antibacterial agent and an antifungal agent. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an arjunolate. It derives from a hydride of an oleanane.
Names & identifiers
- Preferred name
- Arjunolic Acid
- IUPAC
- (4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-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
Arjunolic acid465-00-9(4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-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 acidDTXSID809635838N8Q74HVN3CHEBI:683812,3,23-Trihydroxyolean-12-en-28-oic acidRefChem:114091DTXCID401391327(2alpha,3beta,4alpha)-2,3,23-Trihydroxy-olean-12-en-28-oic acidCHEMBL4644662alpha,3beta,23-trihydroxyolean-12-en-28-oic acid
Show more names
arjunolicaciArjulic acidArjunolic acid, 10 mM in DMSOArjunolic acid >=95% (LC/MS-ELSD)Olean-12-en-28-oicacid, 2,3,23-trihydroxy-, (2a,3b,4a)-hepatocyte 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
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
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
Applications
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.
Suppliers84 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
銘瑞集團有限公司17318633522 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
上海纯优生物科技有限公司15921393123 18302135232 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
合肥翰刚医药科技有限公司
Related reactions
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Compound notes
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