Structure via PubChem · Public domain (PubChem)
crocetin
Sign in to saveAlso known as 8,8'-diapo-psi,psi-carotenedioic acid, 8,8'-diapocarotenedioic acid, 8,8'-diapo-8,8'-carotenedioic acid, trans-crocetin, transcrocetinate, Transcrocetinate, 8,8'-diapo-ψ,ψ-carotenedioic acid
Crocetin is a natural apocarotenoid dicarboxylic acid, a diterpenoid, and a branched-chain dicarboxylic acid. It was the first plant carotenoid to be recognized as early as 1818 while the history of saffron cultivation reaches back more than 3,000 years. The major active ingredient of saffron is the yellow pigment crocin 2 (three other derivatives with different glycosylations are known) containing a gentiobiose (disaccharide) group at each end of the molecule. It is found in the crocus flower together with its glycoside, crocin, and Gardenia jasminoides fruits. It is also known as crocetic ac
Chemical data
- Formula
- C20H24O4
- Molecular weight
- 328.4 g/mol
- IUPAC name
- (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid
- SMILES
- C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)O)/C)/C)/C=C/C=C(/C(=O)O)\C
- InChIKey
- PANKHBYNKQNAHN-MQQNZMFNSA-N
- XLogP
- 5.4
- Polar surface area
- 74.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
760 papers- Crocetin: A Systematic Review.Frontiers in pharmacology · 2021
- Crocetin promotes clearance of amyloid-β by inducing autophagy via the STK11/LKB1-mediated AMPK pathway.Autophagy · 2021
- Crocetin and Crocin from Saffron in Cancer Chemotherapy and Chemoprevention.Anti-cancer agents in medicinal chemistry · 2019
- Crocetin, a versatile carotenoid: Novel insights into pharmacological effects, molecular mechanisms, and therapeutic potential.International immunopharmacology · 2025
- Exploring the therapeutic efficacy of crocetin in oncology: an evidence-based review.Naunyn-Schmiedeberg's archives of pharmacology · 2024
via PubMed
Wikidata facts
- Mass
- 328.167459
Show 4 more facts
- chemical formula
- C₂₀H₂₄O₄
- Commons category
- Crocetin
- canonical SMILES
- CC(=CC=CC=C(C)C=CC=C(C)C(=O)O)C=CC=C(C)C(=O)O
- isomeric SMILES
- C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)O)/C)/C)/C=C/C=C(/C(=O)O)\C
via Wikidata · CC0
~5 min read
Article
6 sectionsContents
- Cell studies
- Physiological effects
- Transcrocetinate sodium
- Mechanism of action
- See also
- References
Crocetin is a natural apocarotenoid dicarboxylic acid, a diterpenoid, and a branched-chain dicarboxylic acid. It was the first plant carotenoid to be recognized as early as 1818 while the history of saffron cultivation reaches back more than 3,000 years. The major active ingredient of saffron is the yellow pigment crocin 2 (three other derivatives with different glycosylations are known) containing a gentiobiose (disaccharide) group at each end of the molecule. It is found in the crocus flower together with its glycoside, crocin, and Gardenia jasminoides fruits. It is also known as crocetic acid. It forms brick red crystals with a melting point of 285 °C.
The chemical structure of crocetin forms the central core of crocin, the compound responsible for the color of saffron. Crocetin is usually extracted commercially from gardenia fruit, due to the high cost of saffron.