138-55-6

Basic information

• Product Name: (4S)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-cyclohexene-1-carbaldehyde
• Synonyms: (4S)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-cyclohexene-1-carbaldehyde;Picrocrocin;(R)-4-(β-D-glucopyranosiloxy)-2,6,6-trimethyl-1-cyclohexene-1-carbaldehyde;(R)-4-(β-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carbaldehyde;Saffron-bitter;Picrocrocine;1-Cyclohexene-1-carboxaldehyde,4-(b-D-glucopyranosyloxy)-2,6,6-triMethyl-,(4R)-;Safranbitter
• CAS NO: 138-55-6
• Molecular Formula: C₁₆H₂₆O₇
• Molecular Weight: 330.37
• Mol File: 138-55-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 196℃ (ethyl acetate )
• Boiling Point: 520.4°Cat760mmHg
• Flash Point: 187.1°C
• Appearance: /
• Density: 1.31±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 5.27E-13mmHg at 25°C
• Refractive Index: 1.561
• PKA: 12.91±0.70(Predicted)
• CAS DataBase Reference: (4S)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-cyclohexene-1-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-cyclohexene-1-carbaldehyde(138-55-6)
• EPA Substance Registry System: (4S)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-cyclohexene-1-carbaldehyde(138-55-6)

Safety Data

• Hazardous Substances Data: 138-55-6(Hazardous Substances Data)

Usage

Description

(4S)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-cyclohexene-1-carbaldehyde is a complex organic compound with a unique molecular structure. It is characterized by its multiple chiral centers and functional groups, which contribute to its potential applications in various fields.

Uses

1. Used in Flavor and Fragrance Industry:
(4S)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-cyclohexene-1-carbaldehyde is used as a flavor compound for its unique and distinct aroma, enhancing the sensory experience of various products.
2. Used in Pharmaceutical Industry:
(4S)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-cyclohexene-1-carbaldehyde is used as a potential therapeutic agent due to its complex structure and chiral centers, which may exhibit specific biological activities.
3. Used in Cosmetic Industry:
(4S)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-cyclohexene-1-carbaldehyde is used as an ingredient in cosmetics for its potential benefits to skin health and its ability to provide a pleasant scent.
4. Used in Research and Development:
(4S)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-cyclohexene-1-carbaldehyde serves as a valuable compound for research purposes, particularly in the fields of organic chemistry, stereochemistry, and drug discovery.
Please note that the specific applications and uses mentioned above are hypothetical and based on the general properties of the compound. Further research and development would be required to fully understand and exploit the potential of (4S)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-cyclohexene-1-carbaldehyde in these industries.

Antitumor activity

Picrocrocin as component of saffron displays same antitumor activity that have great potential for the prevention and treatment of various cancers through affecting cellular DNA and RNA synthesis and free radical scavenging activities of cancer. The experiments results for studying the effect of picrocrocin on proliferation of human tumoral cells (HeLa cell) in vitro showed that picrocrocin have a dose dependent inhibition of cell growth, and doses of picrocrocin inducing 50% inhibition of HeLa cell growth are 3 mM, in which picrocrocin have minor cytotoxicity for normal cells. Thus, picrocrocin can inhibit the growth of cancer cell. Other study results have showed that picrocrocin with highly bioaccessible could be transported quickly and reduced the proliferation of human adenocarcinoma and hepatocarcinoma cells.

InChI:InChI=1/C16H26O7/c1-8-4-9(5-16(2,3)10(8)6-17)22-15-14(21)13(20)12(19)11(7-18)23-15/h6,9,11-15,18-21H,4-5,7H2,1-3H3/t9-,11-,12-,13+,14-,15-/m1/s1

Synthetic route

(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)

Conditions	Yield
With sodium acetate; pyridinium chlorochromate In dimethyl sulfoxide for 16h; Ambient temperature;	10%

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

Conditions	Yield
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 View Scheme

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)

Conditions	Yield
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 View Scheme

(4R)-4-(β-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol-pentaacetat (76686-28-7) → (R)-4-(β-D-glucopyranosyl)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde (138-55-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83.5 percent / Na / methanol / 18 h / Heating 2: 10 percent / Pyridiniumchlorochromat, Natriumacetat / dimethylsulfoxide / 16 h / Ambient temperature View Scheme

[(R)-4-(1-Methoxy-1-methyl-ethoxy)-2,6,6-trimethyl-cyclohex-1-enyl]-methanol (76686-26-5) → (R)-4-(β-D-glucopyranosyl)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde (138-55-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: Et3N / diethyl ether / 1.) 0-5 deg C 2.) rt, 5 h 2: 23 percent / Ag2O, CaSO4 / benzene / 18 h / Heating 3: 83.5 percent / Na / methanol / 18 h / Heating 4: 10 percent / Pyridiniumchlorochromat, Natriumacetat / dimethylsulfoxide / 16 h / Ambient temperature View Scheme

Upstream product

• 76686-29-8 (4R)-4-(β-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol 
• 76686-27-6 (3R)-3-Hydroxy-β-cyclogeranylacetat 
• 76686-28-7 (4R)-4-(β-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol-pentaacetat 
• 76686-26-5 [(R)-4-(1-Methoxy-1-methyl-ethoxy)-2,6,6-trimethyl-cyclohex-1-enyl]-methanol 

Relevant articles and documents

Synthesis of optically active natural carotenoids and structurally related compounds. VI. Synthesis of picrocrocin

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