PROCYANIDIN C1 CAS#: 37064-30-5; ChemWhat Code: 98195

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NamePROCYANIDIN C1
IUPAC Name(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
Molecular StructurePROCYANIDIN-C1-CAS-37064-30-5
CAS Registry Number 37064-30-5
SynonymsProcyanidin C1
37064-30-5
Procyanidol C1
Proanthocyanidin C1
Cinnamtannin A1
Procyanidin trimer C1
(2R,2’R,2”R,3R,3’R,3”R,4R,4’S)-2,2′,2”-Tris(3,4-dihydroxyphenyl)-[4,8′:4′,8”-terchroman]-3,3′,3”,5,5′,5”,7,7′,7”-nonaol
UNII-33516LCW4F
CHEBI:75643
33516LCW4F
EC-(4b,8)-EC-(4b,8)-EC
CHEMBL290632
(2r,2’r,2”r,3r,3’r,3”r,4r,4’s)-2,2′,2”-tris(3,4-dihydroxyphenyl)-3,3′,3”,4,4′,4”-hexahydro-2h,2’h,2”h-4,8′:4′,8”-terchromene-3,3′,3”,5,5′,5”,7,7′,7”-nonol
Epicatechin-(4beta->8)-epicatechin-(4beta->8)-epicatechin
PROCYANIDIN C1, (+)-
DTXSID10190562
[Epicatechin(4b->8)]2-epicatechin
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
(4,8′:4′,8”-Ter-2H-1-benzopyran)-3,3′,3”,5,5′,5”,7,7′,7”-nonol, 2,2′,2”-tris(3,4-dihydroxyphenyl)-3,3′,3”,4,4′,4”-hexahydro-, stereoisomer
[Epicatechin-(4beta->8)]2-epicatechin
(Epicatechin(4b->8))2-epicatechin
Procyanidin C-1
(Epicatechin-(4beta->8))2-epicatechin
C45H38O18
PCC1
SCHEMBL678609
DTXCID50113053
HY-N2342
BDBM50240460
AKOS027321198
AC-35069
MS-31600
1ST166802
CS-0021304
C17624
Q7247556
PROCYANIDIN C1 (CONSTITUENT OF MARITIME PINE)
epicatechin-(4beta-8)-epicatechin-(4beta-8)-epicatechin
PROCYANIDIN C1 (CONSTITUENT OF MARITIME PINE) [DSC]
Epicatechin-(4.beta.–>8)epicatechin-(4.beta.–>8)epicatechin
EPICATECHIN-(4.BETA.->8)-EPICATECHIN-(4.BETA.->8)-EPICATECHIN
(2R,3R,4R,2”R,3”R,4”S,2””R,3””R)-2,2”,2””-Tris-(3,4-dihydroxy-phenyl)-3,4,3”,4”,3””,4””-hexahydro-2H,2”H,2””H-[4,8”;4”,8””]terchromene-3,5,7,3”,5”,7”,3””,5””,7””-nonaol
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-4-yl]chromane-3,5,7-triol
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Molecular FormulaC45H38O18 
Molecular Weight866.8
InChIInChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1
InChI KeyMOJZMWJRUKIQGL-XILRTYJMSA-N
Isomeric SMILESC1[C@H]([C@H](OC2=C1C(=CC(=C2[C@@H]3[C@H]([C@H](OC4=C(C(=CC(=C34)O)O)[C@@H]5[C@H]([C@H](OC6=CC(=CC(=C56)O)O)C7=CC(=C(C=C7)O)O)O)C8=CC(=C(C=C8)O)O)O)O)O)C9=CC(=C(C=C9)O)O)O

Physical Data

AppearanceBrown powder
Description (Association (MCS))Temperature (Association (MCS)), °CPartner (Association (MCS))
Association with compound23.84bovine milk β-lactoglobulin
Association with compound23.84bovine milk α-lactalbumin
Association with compound30.84bovine milk β-lactoglobulin
Association with compound30.84bovine milk α-lactalbumin
Association with compound37.84bovine milk β-lactoglobulin
Association with compound37.84bovine milk α-lactalbumin
Association with compoundbovine serum albumin

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Frequency (NMR Spectroscopy), MHz
Chemical shifts1HCD3OD
Chemical shifts13CCD3OD
Chemical shifts1HCD3OD400
Chemical shifts1HCD3OD-18.16400
Chemical shifts13CCD3OD-18.16100
Description (IR Spectroscopy)Solvent (IR Spectroscopy)
Bandspotassium bromide
Spectrumpotassium bromide
Description (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nm
methanol200, 280
aq. phosphate buffer280
water280
methanol, water281

Route of Synthesis (ROS)

Route of Synthesis (ROS) of PROCYANIDIN C1 CAS# 37064-30-5
Route of Synthesis (ROS) of PROCYANIDIN C1 CAS# 37064-30-5
ConditionsYield
With hydrogen; palladium(II) hydroxide/carbon In tetrahydrofuran; methanol; water under 750.075 Torr; for 1.33333h;

Experimental Procedure
11.A Example 11; Preparation of Epicatechin (4β,8)-Oligomers from Benzyl-Protected Oligomers; A. Preparation of Epicatechin (4β,8)2-Trimer
To a solution of 64.3 mg (33.0 μmol) of bis(5,7,3′,4′-tetra-O-benzyl)epicatechin (4β,8)-dimer in 5 mL of tetrahydrofuran were added 5 mL of methanol, 0.25 mL of water, and 57 mg of 20% Pearlman’s catalyst (Pd(OH)2/C). The mixture was stirred under 1 bar of hydrogen for 80 minutes and filtered over cotton. The filtration residue was washed two times with 10 mL of methanol. The combined filtrates were evaporated, and the residue was taken up in 10 mL of HPLC grade water. The solution was filtered and lyophilized to yield 32.4 mg (101%) of epicatechin (4β,8)2-trimer 6H2O as a fluffy, amorphous, off-white solid: [α]D+70.4°, [α]546+84.40 (MeOH, c 2.2 gL-1); (ref. 4c: [α]D+75.20, acetone, c 8.7 gL-1; ref. 4d: [α]578+90°, MeOH, c 2 gL-1; ref. 6: [α]D+76.40, acetone, c 8.6 gL-1; ref. 19b: []578+920, H2O, c 1.9 gL-1; ref. 19k: [α]D+800, MeOH, c 1.6 gL-1); 13C NMR (CD3OD, TMS; δ 60-85 region only) δ 79.73, 77.08, 73.47, 72.94, 66.84; MS (API/ES) m/z 865.4 (100%; calcd for [M-H]-: 865.2), 577.0 (6%), 288.9 (4%). Analysis: Calculated for C45H38O18.6H2O: C, 55.44; H, 5.17. Found: C, 55.71; H, 5.07.		100%
With hydrogen; palladium dihydroxide In tetrahydrofuran; methanol95%
With hydrogen; palladium dihydroxide In tetrahydrofuran; methanol; water at 20℃; for 1h;95%
With 10 wt% Pd(OH)2 on carbon; hydrogen In tetrahydrofuran; methanol; water at 20℃; for 1h;92%

Safety and Hazards

GHS Hazard StatementsNot Classified
For more detailed information, please visit ECHA C&L website
Source: European Chemicals Agency (ECHA)
License Note: Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: “Source: European Chemicals Agency, http://echa.europa.eu/”. Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
License URL: https://echa.europa.eu/web/guest/legal-notice
Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate
URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446
Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database

Other Data

TransportationUnder the room temperature and away from light
HS Code
StorageUnder the room temperature and away from light
Shelf Life2 years
Market Price
Druglikeness
Lipinski rules component
Molecular Weight866.786
logP3.855
HBA3
HBD15
Matching Lipinski Rules2
Veber rules component
Polar Surface Area (PSA)331.14
Rotatable Bond (RotB)5
Matching Veber Rules1
Use Pattern
Procyanidin C1 CAS 37064-30-5, a complex polyphenolic compound, falls under the larger category of proanthocyanidins which are widely recognized for their potent antioxidant properties. These substances are found in a variety of plants, including fruits, vegetables, nuts, seeds, and bark, playing crucial roles in plant defense mechanisms against pathogens and environmental stressors. Among the diverse array of proanthocyanidins, Procyanidin C1 is particularly notable for its unique structure and significant health-promoting potentials.
Chemically, Procyanidin C1 is a trimer, meaning it consists of three flavonoid units linked together. This structural complexity contributes to its strong antioxidant capacity, surpassing that of simpler flavonoids and even some vitamins known for their antioxidant properties, such as vitamin E and C. The antioxidant activity of Procyanidin C1 is essential in neutralizing free radicals, unstable molecules that can cause oxidative stress leading to cellular damage, aging, and various diseases.
The health benefits associated with Procyanidin C1 are vast and have been the subject of numerous scientific studies. Research has shown that it can support cardiovascular health by improving blood circulation, reducing blood pressure, and preventing the oxidation of low-density lipoprotein (LDL) cholesterol, a key factor in the development of atherosclerosis. Moreover, its anti-inflammatory effects are crucial in mitigating chronic inflammation, a root cause of many chronic conditions, including cancer, diabetes, and neurodegenerative diseases.

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