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Phlorizine

HCID 4789
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
60-81-1
Standard SMILES
O=C(CCc1ccc(O)cc1)c1c(O)cc(O)cc1OC1OC(CO)C(O)C(O)C1O
InChIKey
IOUVKUPGCMBWBT-UHFFFAOYSA-N
Molecular formula
C21H24O10
Average molar mass
436.4 g/mol
Monoisotopic mass
436.13694696

Overview

Phlorizine is a glycoside and a member of flavonoids.

Names & identifiers

Preferred name
Phlorizine
IUPAC
1-[2,4-dihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
English name
Phlorizin
Molecular formula
C21H24O10
Molecular weight
436.41

Names & synonyms

Phlorizine1-[2,4-dihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one1-(2,4-dihydroxy-6-(3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyphenyl)-3-(4-hydroxyphenyl)propan-1-oneRefChem:1095072NSC2833PhloridizinNSC 2833s2343CHEMBL45266SCHEMBL113699CHEBI:182131IOUVKUPGCMBWBT-UHFFFAOYSA-N
Show more names
PHLORIDZINphlorhizinphloridzinePHLORIDZIN DIHYDRATEFloridzinPHLORIZINPhlorininphlorrhizin
BDBM237198HMS3656K07NCI60_002323DB-0500991-Propanone,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-[2,4-dihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-3-(4-hydroxyphenyl)propan-1-one

Database identifiers

CAS
60-81-1

Properties

Computed structural properties

XLogP
1.2
Topological polar surface area
177 Ų
Hydrogen bond donors
7
Hydrogen bond acceptors
10
Rotatable bonds
7
Heavy atoms
31
Formal charge
0
Complexity
581

Physicochemical properties

Melting point
113 · 113-114 °C(lit.)
Boiling point
468.89 °C · 468.89°C (rough estimate)
Density
1.3178 · 1.3178 (rough estimate)
refractive index
-54 ° · -54 ° (C=3.2, 95% EtOH)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature
solubility
DMSO (Slightly), Methanol (Slightly)
form
Solid
pka
7.15 · 7.15±0.40(Predicted)
color
Light Yellow to Tan
Merck
14 · 14,7327
Major Application
food and beverages
Cosmetics Ingredients Functions
SKIN CONDITIONING
InChIKey
IOUVKUPGCMBWBT-LKLLPNDVNA-N
SMILES
C(C1C(=CC(O)=CC=1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)(=O)CCC1C=CC(O)=CC=1 |&1:9,10,11,13,15,r|
LogP
0.452 · 0.452 (est)

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

F
3-10-23
wgk
3
rtecs
UC2080000
hs_code
29389090
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
REACH Registrations
Active
Precautionary statements
P261-P305+P351+P338

Chemistry & industry

Applications · 3 items

UsesIt is a dihydrochalcone occurring in all parts of the apple tree except the mature fruit. Once thought to occur in pear, plum, cherry trees and other Rosaceae

Usesinduces experimental glucosuria, antifeedant

UsesSodium-glucose cotransporter 1 (SGLT1) is a high affinity, low capacity transporter abundant in the small intestine, with some expression in the kidney as well. SGLT2 is a low affinity, high capacity transporter in the kidney that accounts for approximately 90% of glucose reabsorption into the blood stream. Selective inhibition of SGLT2 is a potential strategy for reducing plasma glucose levels as a treatment for diabetes. Phlorizin is a natural product, first isolated from the bark of apple trees, that reduces plasma glucose levels by blocking renal and intestinal glucose absorption through inhibition of SGLT1 and SGLT2. It competitively inhibits the initial rate of a-methyl-D-glucopyranoside (a-MDG) uptake in human COS-1 cells expressing hSGLT1 and hSGLT2 with IC50 values of 400 and 65 nM, respectively. In HEK293T cells expressing human SGLT1 and SGLT2, phlorizin exhibits Ki values of 140 and 11 nM, respectively, at 37°C.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
南京丙承生物科技有限公司18805194892 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]

Related reactions

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New reaction record

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
4789
ChEMBL
CHEMBL45266
ChEBI
CHEBI:182131
Nikkaji
J3.240.547I
CAS DataBase Reference
60 · 60-81-1(CAS DataBase Reference)
FDA UNII
9 S17279X · CU9S17279X
EPA Substance Registry System
Phlorizin (60-81-1)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36
WGK Germany
3 · 3
RTECS
2080000 · UC2080000
F
3 · 3-10-23
HS Code
29389090 · 29389090
Storage Class
11 · 11 - Combustible Solids
REACH Registrations
Active
大连美仑生物技术有限公司
0411-62910999 13889544652 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
上海融禾医药科技发展有限公司17301719108 13341702378 · [email protected]
深圳虹彩祥根生物科技有限公司+86-0755-89668383 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
长沙上禾生物科技有限公司0731-84213302 18975842720 · [email protected]
南京春秋生物工程有限公司17388075642 13815430202 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
成都健腾生物技术有限公司86-28-85159085 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
西安康培基生物科技有限公司86-029-85456576 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
陕西帕尼尔生物科技有限公司13720616393;029-84385017-8003 13720616393 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海喀露蓝科技有限公司18149758185 18149758185 · [email protected]
上海湄水化工科技有限公司021-60549325 18616193163
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
上海鑫圭生物科技有限公司15121041756 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
上海洽凡生化科技有限公司+86-021-61654350 · [email protected]
江苏艾康生物医药研发有限公司025-66028182 17714375163 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]

Additional notes

DefinitionChEBI: An aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 2' via a glycosidic linkage.