CAPSANTHIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C40H56O3
Molecular Weight	584.8708
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	9
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(\C=C\C=C(C)\C=C\C(=O)[C@]1(C)C[C@@H](O)CC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C[C@@H](O)CC2(C)C

InChI

InChIKey=VYIRVAXUEZSDNC-RDJLEWNRSA-N

InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37(43)40(10)28-35(42)27-39(40,8)9/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t34-,35+,40+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C40H56O3
Molecular Weight	584.8708
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	9
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11566483 | https://www.ncbi.nlm.nih.gov/pubmed/28449555 | http://www.ivyroses.com/Define/E160c

Capsanthin, the red xanthophyll pigment, is used as a food additive approved by the European Union (EU) under the name as E160c. The common names for E160c are paprika extract, capsanthin or capsorubin. Capsanthin shows potent anti-adipogenic, lipolytic and fatty acid burning activities due to its potent adrenoceptor-beta2-agonistic activity. It was revealed, that capsanthin was not a thermogenic substance that is why it may be a good candidate for the development of new bioactive agent effective as a new anti-obese or insulin sensitivity enhancing substance.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 203 Target ID: P07550\|\|\|Q53GA6\|\|\|Q9UCZ3 Gene ID: 154.0 Gene Symbol: ADRB2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28449555	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28449555	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Accumulation and clearance of capsanthin in blood plasma after the ingestion of paprika juice in men.	1997 Aug	9237940
Carotenoids in human blood plasma after ingesting paprika juice.	2000 May	10879492
[Spectral characterization for capsanthin molecule with in vitro oxidative defense reaction].	2014 Feb	24822401
Carotenoids exclusively synthesized in red pepper (capsanthin and capsorubin) protect human dermal fibroblasts against UVB induced DNA damage.	2016 Aug 31	27537377
In vivo and in vitro evaluation for nutraceutical purposes of capsaicin, capsanthin, lutein and four pepper varieties.	2016 Dec	27746329
Capsanthin Inhibits both Adipogenesis in 3T3-L1 Preadipocytes and Weight Gain in High-Fat Diet-Induced Obese Mice.	2017 May 1	28449555

Patents

Sample Use Guides

In Vivo Use Guide

Supplementing capsanthin-rich paprika juice for 1 wk (equivalent to three doses of 5.4 micromol capsanthin/d; 16.2 micromol/d), the level of capsanthin reached a plateau (0.10-0.12 micromol/L) between d 2 and 7 and was not detectable by d 16.

Route of Administration: Oral

In Vitro Use Guide

Capsanthin Inhibits adipogenesis in 3T3-L1 preadipocytes. During adipogenesis in 3T3-L1 preadipocytes, capsanthin (10 uM) inhibited adipogenesis (IC₅₀; 2.5 μM) and also showed lipolytic activity in differentiated adipocytes from the preadipocytes (ED₅₀; 872 nM). It was found, that the pharmacological activity of capsanthin on adipogenesis in 3T3-L1 was mainly due to its adrenoceptor-β₂-agonistic activity

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:39:40 GMT 2023` Edited by `admin` on `Fri Dec 15 20:39:40 GMT 2023`
Record UNII	420NY1J57N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CAPSANTHIN

Common Name

English

CAPSANTHIN/CAPSORUBIN [INCI]

Common Name

English

CAPSANTHIN/CAPSORUBIN

Official Name

English

3,3'-DIHYDROXY-.BETA.,.KAPPA.-CAROTEN-6'ON

Common Name

English

(3R,3'S,5'R)-3,3'-DIHYDROXY-.BETA.,.KAPPA.-CAROTEN-6'-ONE

Common Name

English

.BETA.,.KAPPA.-CAROTEN-6'ONE, 3,3'DIHYDROXY-

Common Name

English

ALL-TRANS-CAPSANTHIN

Common Name

English

2,4,6,8,10,12,14,16,18-NONADECANONAEN-1-ONE, 19-(4-HYDROXY-2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-1-(5-HYDROXY-1,2,2-TRIMETHYLCYCLOPENTYL)-4,8,13,17-TETRAMETHYL-

Systematic Name

English

CAPSANTHIN [MI]

Common Name

English

2,4,6,8,10,12,14,16,18-NONADECANONAEN-1-ONE, 19-(4-HYDROXY-2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-1-(4-HYDROXY-1,2,2-TRIMETHYLCYCLOPENTYL)-4,8,13,17-TETRAMETHYL-, (ALL-E)-

Common Name

English

Code System Code Type Description

PUBCHEM

5281228