Alphitolic acid - ≥97% , CAS No.19533-92-7

CAS: 19533-92-7 Cat. No.: A648523 Peso molecular: 472.70 PubChem CID: 12305768
Disponible para pedir
GRADE & PURITY ≥97%
Synonyms
2alpha-Hydroxybetulinic acid | Lup-20(29)-en-28-oic acid, 2,3-dihydroxy- (8CI); (2,3)-2,3-Dihydroxylup-20(29)-en-28-oic acid; 3aH-Cyclopenta[a]chrysene, lup-20(29)-en-28-oic acid deriv.; 2-Hydroxybetulinic acid; Alphitolic acid | AKOS032948680 | CHEBI:676
Storage
Protected from light,Store at -80°C
Shipped In
Dry ice packs + Cold packs
 ·  off list, applied to all prices below.
Size
Estado
Price
Qty
1mg
A648523-1mg
8-12 wks(?) Production requires sourcing of materials. We appreciate your patience and understanding.
760,90US$
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Why this grade

≥97% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Protected from light,Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Descripción general

Alphitolic acid (Aophitolic acid) is an anti-inflammatory triterpene could found in quercus aliena. Alphitolic acid blocks Akt–NF-κB signaling to induce apoptosis. Alphitolic acid induces autophagy. Alphitolic acid has anti-inflammatory activity and down-regulates the NO and TNF-α production. Alphitolic acid can be used for cancer and inflammation research .

In Vitro

Alphitolic acid (Aophitolic acid) (0-30 µM; 72 hours; HSC-3, SCC2095, and SCC4 cells) has anti-proliferative activity in oral cancer cells in a dose-dependent manner, induces apoptosis and blocks Akt–NF-κB signaling. Alphitolic acid (Aophitolic acid) (0-25 µM; 3-72 hours; SCC4 cells) induces autophagy with increases the expression of autophagosome marker LC3B-II and two autophagyregulatory proteins. Alphitolic acid (Aophitolic acid) (0-25 µM; 72 hours; SCC4 cells) increases p53 phosphorylation and expression, decreases in the expression of the oncogenic E3 ligase MDM2. Alphitolic acid (Aophitolic acid) (0-25 µM; 72 hours; RAW 264.7 macrophages) has anti-inflammatory activity and down-regulates the NO and TNF-α production with IC 50 values of 17.6 and 22.7 µM, respectively. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: HSC-3, SCC2095 and SCC4 cells Concentration: 0, 10, 15, 20, 25 and 30 µM Incubation Time: 72 hours Result: Suppressed the proliferation of SCC4 and SCC2095 cells with IC 50 values of 12 and 15 µM, respectively. Apoptosis AnalysisCell Line: SCC4 cells Concentration: 0, 10, 20 and 30 µM Incubation Time: 72 hours Result: Increased the percentage of apoptotic cells from 11.8% to 25.1% in a dose-dependent manner. Western Blot AnalysisCell Line: SCC4 cells Concentration: 0, 10, 15 and 20 µM Incubation Time: 72 hours Result: Decreased the expression of phosphorylation of Akt and its downstream substrates, including p70S6K, S6, and IκBα. Down-regulated the expression of NF-κB and its downstream target gene product Bcl-2. Western Blot AnalysisCell Line: SCC4 cells Concentration: 0, 10, 15, 20 and 25 µM Incubation Time: 3, 6, 12, 24, 48 and 72 hours Result: Increased autophagosome marker LC3B-II in a dose- and time-dependent manner. Increased the expression of autophagy-related protein 7 (Atg7).

In Vivo

Alphitolic acid (Aophitolic acid) (47-756 µg/ear; i.h.; adult male CF-1 mice) has anti-inflammatory activity in vivo. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Adult male CF-1 miceDosage: 47, 94, 330, 378 and 756 µg/ear Administration: subcutaneous injection Result: Had anti-inflammatory activity with an ED 50 of 0.11 and 0.20 µM in a dose-dependent.

Form:Solid

Specifications

Sinónimos
2alpha-Hydroxybetulinic acid | Lup-20(29)-en-28-oic acid, 2, 3-dihydroxy- (8CI); (2, 3)-2, 3-Dihydroxylup-20(29)-en-28-oic acid; 3aH-Cyclopenta[a]chrysene, lup-20(29)-en-28-oic acid deriv.; 2-Hydroxybetulinic acid; Alphitolic acid | AKOS032948680 | CHEBI:676
Especificaciones y pureza
≥97%
Mecanismos bioquímicos y fisiológicos
Alphitolic acid (Aophitolic acid) is an anti-inflammatory triterpene could found in quercus aliena. Alphitolic acid blocks Akt–NF-κB signaling to induce apoptosis . Alphitolic acid induces autophagy . Alphitolic acid has anti-inflammatory activity and dow
Condiciones de almacenamiento de almacenamiento
Protected from light, Store at -80°C
Enviado en
Dry ice packs + Cold packs
Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.
Tipo de acción
INHIBITOR
Pureza
≥97%
Nombres e identificadores
Sonrisas canónicasCC(=C)C1CCC2(C1C3CCC4C(C3(CC2)C)(CCC5C4(CC(C(C5(C)C)O)O)C)C)C(=O)O
IUPAC Name(1R,3aS,5aR,5bR,7aR,9R,10R,11aR,11bR,13aR,13bR)-9,10-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
InChIKeyPFCVZKFJHRCLCC-PGOIBATFSA-N
INCHI1S/C30H48O4/c1-17(2)18-10-13-30(25(33)34)15-14-28(6)19(23(18)30)8-9-22-27(5)16-20(31)24(32)26(3,4)21(27)11-12-29(22,28)7/h18-24,31-32H,1,8-16H2,2-7H3,(H,33,34)/t18-,19+,20+,21-,22+,23+,24-,27-,28+,29+,30-/m0/s1
Isómeros SMILES CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@H]4[C@]([C@@]3(CC2)C)(CC[C@@H]5[C@@]4(C[C@H]([C@@H](C5(C)C)O)O)C)C)C(=O)O
CAS alternativo 19533-92-7
PubChem CID 12305768
Términos de entrada MeSH alphitolic acid
Peso molecular 472.70

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

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✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

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📊 Datasheet

Quick-reference summary of product specifications and applications.

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🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

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Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClasePrenol lipids
SubclassTriterpenoids
Intermediate Tree Nodes Not available
Direct ParentTriterpenoids
Alternative Parents 18-hydroxysteroids  Oxosteroids  Secondary alcohols  Cyclic alcohols and derivatives  1,2-diols  Monocarboxylic acids and derivatives  Carboxylic acids  Organic oxides  Hydrocarbon derivatives  Carbonyl compounds  
Molecular FrameworkAliphatic homopolycyclic compounds
Substituents Triterpenoid - 18-hydroxysteroid - 18-oxosteroid - Hydroxysteroid - Oxosteroid - Steroid - Cyclic alcohol - 1,2-diol - Secondary alcohol - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxide - Alcohol - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Aliphatic homopolycyclic compound
DescripciónThis compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
External Descriptors dihydroxy monocarboxylic acid - pentacyclic triterpenoid
Estructura 3D
Modelo de Estructura Química Interactiva





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Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
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OVCAR-3 (48710 Activities)
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PANC-1 (6144 Activities)
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H9 (1832 Activities)
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MDA-MB-435 (38290 Activities)
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MDA-MB-231 (73002 Activities)
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RELA Tchem Nuclear factor NF-kappa-B p65 subunit (627 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLI1 Tchem Zinc finger protein GLI1 (201 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Objetivos asociados (no humanos)
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Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
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Influenza A virus (11224 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LLC-PK1 (2135 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDCK (10148 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BV-2 (3710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mecanismos de acción
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular472.700 g/mol
XLogP37.200
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass472.355 Da
Monoisotopic Mass472.355 Da
Topological Polar Surface Area77.800 Ų
Heavy Atom Count34
Formal Charge0
Complexity894.000
Isotope Atom Count0
Defined Atom Stereocenter Count11
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Calculadoras de soluciones
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