Friedelin - ≥98% , CAS No.559-74-0

CAS: 559-74-0 Cat. No.: F331475 Molecular Weight: 426.72 Beilstein Registry Number: 1916451 EC Number: 209-205-1

GRADE & PURITY ≥98%

Synonyms

24,25,26-Trinoroleanan-3-one, 5,9,13-trimethyl-,(4b,5b,8a,9b,10a,13a,14b)- | Friedelan-3-one | SR-05000002227-3 | 3-friedelanone | CHEBI:5171 | NSC 55141 | 3-OXOFRIEDELANE | Friedelin, technical grade | C08626 | Maybridge1_008581 | 3(2H)-PICENONE, EICOSAH

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Friedelin is a triterpene natural product isolated from the|Quercus suber|L. cork tree bark. Friedelin is the most abundant triterpene in extracts isolated from this tree. Friedelin has been described along with similar triterpenes in studying inhibitors of photosynthesis for use as herbicides, and has been described to have antifungal and antimicrobial properties.

Product Application:

Friedelin is the major triterpene constituent of cork extracts

Specifications

Synonyms

24, 25, 26-Trinoroleanan-3-one, 5, 9, 13-trimethyl-, (4b, 5b, 8a, 9b, 10a, 13a, 14b)- | Friedelan-3-one | SR-05000002227-3 | 3-friedelanone | CHEBI:5171 | NSC 55141 | 3-OXOFRIEDELANE | Friedelin, technical grade | C08626 | Maybridge1_008581 | 3(2H)-PICENONE, EICOSAH

Specifications & Purity

≥98%

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504756060
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756060
• Canonical Smiles: CC1C(=O)CCC2C1(CCC3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C)C)C)C)C)C
• IUPAC Name: (4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bS)-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
• InChIKey: OFMXGFHWLZPCFL-SVRPQWSVSA-N
• INCHI: 1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22+,23-,24+,26+,27+,28-,29+,30-/m0/s1
• Isomeric SMILES: C[C@H]1C(=O)CC[C@@H]2[C@@]1(CC[C@H]3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C)C)C)C)C
• WGK Germany: 3
• Molecular Weight: 426.72
• Beilstein: 1916451
• Reaxy-Rn: 2063030
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2063030&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Triterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Triterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Triterpenoids
• Alternative Parents: Cyclic ketones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Triterpenoid - Cyclic ketone - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
• External Descriptors: Hopanes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ACHE Tclin Acetylcholinesterase (18204 Activities)

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NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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MCF7 (126967 Activities)

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SK-OV-3 (52876 Activities)

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TK-10 (45540 Activities)

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UACC-62 (47335 Activities)

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A549 (127892 Activities)

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HepG2 (196354 Activities)

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NCI-H460 (60772 Activities)

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SF-268 (49410 Activities)

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GPBAR1 Tchem G-protein coupled bile acid receptor 1 (1723 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

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Associated Targets(non-human)

Nos2 Nitric oxide synthase, inducible (3573 Activities)

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Spinacia oleracea (250 Activities)

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Hepatitis B virus (7925 Activities)

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RAW264.7 (28094 Activities)

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BCHE Cholinesterase (8742 Activities)

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Phytophthora cactorum (113 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (partly), chloroform (1:8), and alcohol (1:250).
• Sensitivity: Moisture sensitive；light sensitive
• Refractive Index: n20D1.50 (Predicted)
• Specific Rotation[α]: α20D-12°±3°, c = 1 in chloroform
• Boil Point(°C): ~477.2° C at 760 mmHg (Predicted)
• Melt Point(°C): 262-265° C (lit.)
• Molecular Weight: 426.700 g/mol
• XLogP3: 9.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 426.386 Da
• Monoisotopic Mass: 426.386 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 781.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yadan Chen, Yanbin Wang, Liang He, Liling Wang, Jianchen Zhao, Zhenya Yang, Qin Li, Rui Shi.  (2024)  Supercritical CO2 Extraction of Terpenoids from Indocalamus latifolius Leaves: Optimization, Purification, and Antioxidant Activity.  Foods,  13  (11): (1719).  [PMID:38890947] [10.3390/foods13111719]