Basic information
- CAS
2957-21-3- Standard SMILES
COc1cc(O)c2c(c1)O[C@H](c1ccc(O)cc1)CC2=O- InChIKey
DJOJDHGQRNZXQQ-AWEZNQCLSA-N- Molecular formula
- C16H14O5
- Average molar mass
- 286.28 g/mol
- Monoisotopic mass
- 286.08412354
Overview
Sakuranetin is a flavonoid phytoalexin that is (S)-naringenin in which the hydroxy group at position 7 is replaced by a methoxy group. It has a role as an antimycobacterial drug and a plant metabolite. It is a member of 4'-hydroxyflavanones, a (2S)-flavan-4-one, a monomethoxyflavanone, a dihydroxyflavanone and a flavonoid phytoalexin. It is functionally related to a (S)-naringenin.
Names & identifiers
- Preferred name
- Sakuranetin
- IUPAC
- (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
- English name
- Sakuranetin
- Molecular formula
- C16H14O5
- Molecular weight
- 286.28
Names & synonyms
Sakuranetin2957-21-3(2S)-sakuranetinNaringenin 7-methyl ether5,4'-Dihydroxy-7-methoxyflavanone(S)-(-)-4',5-dihydroxy-7-methoxyflavanone5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chroman-4-one3O38P61299CHEBI:289274H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-, (S)-(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychroman-4-oneDTXSID10874774
Show more names
Nsc 407228SAKURANETIN(P)SAKURANETIN(SH)Sakura PavilionSAKURANETIN hplcEinecs 220-980-5(-)-(S)-sakuranetinSakrinak? Sakuranetin
RefChem:180866DTXCID901012899(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one220-980-5(S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychroman-4-one4',5-Dihydroxy-7-methoxyflavanone7-O-Methylnaringenin4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-, (2S)-
Database identifiers
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 76 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 377
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214]
Melting Point152 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 153 · 153-154°C
- alpha
- 16 · D16 +8.0° (c = 7.92 in acetone); D12 +8.4° (c = 6.28 in methanol)
- Boiling point
- 555.9 · 555.9±50.0 °C(Predicted)
- Density
- 1.37 · 1.370±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Store at 2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 7.42 · 7.42±0.40(Predicted)
- form
- Solid
- color
- White to Off-White
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
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- Hazard statements
- H302
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
UsesSakuranetin is a flavanone phytoalexin reported to play an important role in disease resistance in rice plants. Antifungal and antimicrobial activity.
Suppliers101 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]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
郑州汇聚化工有限公司0371-53399770 18037166334 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [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+8618062405514 · [email protected]
成都健腾生物技术有限公司028-85159085 18080455027 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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