Picrocrocin

Base Information

• Chemical Name: Picrocrocin
• CAS No.: 138-55-6
• Molecular Formula: C16H26 O7
• Molecular Weight: 330.378
• UNII: ON5B022511
• DSSTox Substance ID: DTXSID40160450
• Nikkaji Number: J5.635I
• Wikipedia: Picrocrocin
• Wikidata: Q289866
• Metabolomics Workbench ID: 58578
• Mol file: 138-55-6.mol

Synonyms:4-(beta-D-glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde;picrocrocin

Chemical Property of Picrocrocin

Chemical Property:

• Vapor Pressure: 5.27E-13mmHg at 25°C
• Melting Point: 196℃ (ethyl acetate )
• Boiling Point: 520.4°Cat760mmHg
• PKA: 12.91±0.70(Predicted)
• Flash Point: 187.1°C
• PSA: 116.45000
• Density: 1.31g/cm³
• LogP: -0.49310
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 330.16785316
• Heavy Atom Count: 23
• Complexity: 473

Purity/Quality:

≥98% ^*data from raw suppliers

Picrocrocin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CC(C1)OC2C(C(C(C(O2)CO)O)O)O)(C)C)C=O
• Isomeric SMILES: CC1=C(C(C[C@@H](C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)(C)C)C=O
• Description: Picrocrocin, composing of safranal and glycoside, is one major compounds of saffron (Crocus sativus L. stigma), responsible for the bitter taste of saffron and a molecular marker of this spice, whose taste cannot be imitated from other spices or seasonings, and it can serve to identify true saffron. Saffron possesses various therapeutic activities such as antihypertensive, anticonvulsant, antitussive, antigenototoxic, anticancer, cytotoxic effects, anxiolytic, antioxidant, antidepressant, anti-inflammatory, and relaxant activity. As major bioactive compounds of saffron, picrocrocin also has some valuable medicinal properties similar as saffron, especially anticancer effect.
• Uses: Picrocrocin is a secondary metabolite of Saffron and has been found to be the taste component of saffron.

Technology Process of Picrocrocin

There total 5 articles about Picrocrocin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 10.0%

(4R)-4-(β-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol (76686-29-8) → (R)-4-(β-D-glucopyranosyl)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde (138-55-6)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dimethyl sulfoxide; for 16h; Ambient temperature;

DOI:10.1002/hlca.19800630616

Reference yield:

(3R)-3-Hydroxy-β-cyclogeranylacetat (76686-27-6) → (R)-4-(β-D-glucopyranosyl)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde (138-55-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 23 percent / Ag₂O, CaSO₄ / benzene / 18 h / Heating

2: 83.5 percent / Na / methanol / 18 h / Heating

3: 10 percent / Pyridiniumchlorochromat, Natriumacetat / dimethylsulfoxide / 16 h / Ambient temperature

With calcium sulfate; sodium acetate; sodium; pyridinium chlorochromate; silver(l) oxide; In methanol; dimethyl sulfoxide; benzene;

DOI:10.1002/hlca.19800630616

Reference yield:

Isopropenyl (IPM)-Aether des (3R)-3-Hydroxy-β-cyclocitral → (R)-4-(β-D-glucopyranosyl)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde (138-55-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 23.5 g / NaBH₄ / propan-2-ol / 1.) 0-5 deg C 2.) rt, 3 h

2: Et₃N / diethyl ether / 1.) 0-5 deg C 2.) rt, 5 h

3: 23 percent / Ag₂O, CaSO₄ / benzene / 18 h / Heating

4: 83.5 percent / Na / methanol / 18 h / Heating

5: 10 percent / Pyridiniumchlorochromat, Natriumacetat / dimethylsulfoxide / 16 h / Ambient temperature

With calcium sulfate; sodium tetrahydroborate; sodium acetate; sodium; triethylamine; pyridinium chlorochromate; silver(l) oxide; In methanol; diethyl ether; dimethyl sulfoxide; isopropyl alcohol; benzene;

DOI:10.1002/hlca.19800630616

upstream raw materials:

(4R)-4-(β-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol

(3R)-3-Hydroxy-β-cyclogeranylacetat

(4R)-4-(β-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol-pentaacetat

[(R)-4-(1-Methoxy-1-methyl-ethoxy)-2,6,6-trimethyl-cyclohex-1-enyl]-methanol

Refernces