madecassic acid
urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2a,3b,4a,6b)-
 
Notes:
Constit. of Centella asiatica (Asiatic pennywort)
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      Product(s):
      18449-41-7 Madecassic acid >98%
      Madecassic acid is a natural triterpenoid found in the herbs of Centella asiatica (L.) Urban. Madecassic acid has strong metabolic capacity.
       
       
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CAS Number: 18449-41-7Picture of molecule3D/inchi
FDA UNII: M7O1N24J82
Nikkaji Web: J39.267G
MDL: MFCD00895441
XlogP3-AA: 4.40 (est)
Molecular Weight: 504.70776000
Formula: C30 H48 O6
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
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Google Scholar: with word "odor"Search
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PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 641.65 °C. @ 760.00 mm Hg (est)
Flash Point: 673.00 °F. TCC ( 355.90 °C. ) (est)
logP (o/w): 4.321 (est)
Soluble in:
 water, 0.9738 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: skin conditioning
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Suppliers:
Alfa Biotechnology
For experimental / research use only.
Madecassic acid 98%
BOC Sciences
For experimental / research use only.
Madecassic acid >98%
Odor: characteristic
Use: Madecassic acid is a natural triterpenoid found in the herbs of Centella asiatica (L.) Urban. Madecassic acid has strong metabolic capacity.
Changsha Organic Herb
Centella asiatica Extract
Santa Cruz Biotechnology
For experimental / research use only.
Madecassic Acid ≥95%
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: cosmetic agents
Recommendation for madecassic acid usage levels up to:
 not for fragrance use.
 
Recommendation for madecassic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 73412
National Institute of Allergy and Infectious Diseases: Data
 (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Chemidplus: 0018449417
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References:
 (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 73412
Pubchem (sid): 135033173
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
HMDB (The Human Metabolome Database): HMDB36670
FooDB: FDB015600
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 guava fruit
Search Trop  Picture
 pennywort asiatic pennywort
Search Trop  Picture
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Synonyms:
 brahmic acid
(1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
 urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2a,3b,4a,6b)-
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Articles:
PubMed: Metabolomic analysis of methyl jasmonate-induced triterpenoid production in the medicinal herb Centella asiatica (L.) urban.
PubMed: [Studies on fingerprints of Centella asiatica by HPLC].
PubMed: Two new triterpene glycosides from Centella asiatica.
PubMed: Madecassic acid inhibits the mouse colon cancer growth by inducing apoptosis and immunomodulation.
PubMed: Asiaticoside, a component of Centella asiatica, inhibits melanogenesis in B16F10 mouse melanoma.
PubMed: Centella asiatica in dermatology: an overview.
PubMed: Metabolomic analysis of methyl jasmonate-induced triterpenoid production in the medicinal herb Centella asiatica (L.) urban.
PubMed: [Simultaneous determination of madecassoside,asiaticoside and their aglycones in Centella asiatica (L.) urban extracts by RP-HPLC].
PubMed: Identification of Major Active Ingredients Responsible for Burn Wound Healing of Centella asiatica Herbs.
PubMed: Factors affecting the content of pentacyclic triterpenes in Centella asiatica raw materials.
PubMed: Titrated extract of Centella asiatica provides a UVB protective effect by altering microRNA expression profiles in human dermal fibroblasts.
PubMed: Centella asiatica attenuates the neurobehavioral, neurochemical and histological changes in transient focal middle cerebral artery occlusion rats.
PubMed: Bioavailability, distribution, and antioxidative effects of selected triterpenes in mice.
PubMed: [Studies on fingerprints of Centella asiatica by HPLC].
PubMed: Triterpene composition and bioactivities of Centella asiatica.
PubMed: Two new triterpene glycosides from Centella asiatica.
PubMed: Pentacyclic triterpenoids from the medicinal herb, Centella asiatica (L.) Urban.
PubMed: Conversion of alpha-amyrin into centellosides by plant cell cultures of Centella asiatica.
PubMed: Anti-inflammatory effects of madecassic acid via the suppression of NF-kappaB pathway in LPS-induced RAW 264.7 macrophage cells.
PubMed: An improved HPLC-UV method for the simultaneous quantification of triterpenic glycosides and aglycones in leaves of Centella asiatica (L.) Urb (APIACEAE).
PubMed: Triterpenoid saponin content and the expression level of some related genes in calli of Centella asiatica.
PubMed: Association (micellization) and partitioning of aglycon triterpenoids.
PubMed: Incorporation of triterpenic derivatives within an o/w/o multiple emulsion: structure and release studies.
PubMed: Molecular dynamics simulation and thermodynamic modeling of the self-assembly of the triterpenoids asiatic acid and madecassic acid in aqueous solution.
PubMed: [Separation and determination of madecassic acid in triterpenic genins of Centella asiatica by high performance liquid chromatography using beta-cyclodextrin as mobile phase additive].
PubMed: Identification of triterpenoid compounds of Centella asiatica by thin-layer chromatography and mass spectrometry.
PubMed: Advanced formulation and pharmacological activity of hydrogel of the titrated extract of C. asiatica.
PubMed: Gene expression changes in the human fibroblast induced by Centella asiatica triterpenoids.
PubMed: An improved HPLC method for quantitative determination of six triterpenes in Centella asiatica extracts and commercial products.
PubMed: Medicinal foodstuffs. XXVII. Saponin constituents of gotu kola (2): structures of new ursane- and oleanane-type triterpene oligoglycosides, centellasaponins B, C, and D, from Centella asiatica cultivated in Sri Lanka.
PubMed: New innovations in scar management.
PubMed: Pharmacokinetics and tissue distribution of betulinic acid in CD-1 mice.
PubMed: Triterpenes from Centella asiatica stimulate extracellular matrix accumulation in rat experimental wounds.
PubMed: Quantitative determination of triterpenes in extracts and phytopreparations of Centella asiatica (L.) urban.
PubMed: Influence of asiatic acid, madecassic acid, and asiaticoside on human collagen I synthesis.
PubMed: Centella asiatica (Indian pennywort), an effective therapeutic but a weak sensitizer.
PubMed: Stimulation of collagen synthesis in fibroblast cultures by a triterpene extracted from Centella asiatica.
PubMed: Contact dermatitis due to madecassol.
PubMed: The metabolism of asiatic acid,-madecassic acid and asiaticoside in the rat.
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