5056-17-7

Basic information

• Product Name: (E,E,E)-2,7-dimethylocta-2,4,6-trienedial
• Synonyms: (E,E,E)-2,7-dimethylocta-2,4,6-trienedial;2,7-Dimethyl-2,4,6-octatriendial;2,7-Dimethylocta-2,4,6-trienedial;(2E,4E,6E)-2,7-Dimethyl-2,4,6-octatrienedial;Einecs 225-756-0;2,7-Dimethyl-2,4,6-Octatrienedial;(all-E)-2,7-Dimethyl-2,4,6-octatrienedial;(E,E,E)-2,7-Dimethyl-2,4,6-octatrien-1,8-dial
• CAS NO: 5056-17-7
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20108
• EINECS: 225-756-0
• Mol File: 5056-17-7.mol
• Article Data: 25

Chemical Properties

• Melting Point: 162-163.5℃ (methanol )
• Boiling Point: 90-94℃ (10 Torr)
• Flash Point: 113.3 °C
• Appearance: /
• Density: 0.973 g/cm³
• Vapor Pressure: 0.000939mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform, Methanol (Slightly)
• Stability: Air Sensitive
• CAS DataBase Reference: (E,E,E)-2,7-dimethylocta-2,4,6-trienedial(CAS DataBase Reference)
• NIST Chemistry Reference: (E,E,E)-2,7-dimethylocta-2,4,6-trienedial(5056-17-7)
• EPA Substance Registry System: (E,E,E)-2,7-dimethylocta-2,4,6-trienedial(5056-17-7)

Safety Data

• Hazardous Substances Data: 5056-17-7(Hazardous Substances Data)

Usage

Uses

2,7-Dimethylocta-2,4,6-triene-1,8-dial is a part of electrophilic carotenoid derivative that contributes to cancer prevention as well as in bone health maintenance through the inhibition of NFkB transcription system.

InChI:InChI=1/C10H12O2/c1-9(7-11)5-3-4-6-10(2)8-12/h3-8H,1-2H3/b4-3+,9-5+,10-6+

Synthetic route

2,2'-(1,6-Dimethyl-1,3,5-hexatrienylen)bis(5,5-dimethyl-1,3-dioxan) (209615-09-8) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 20℃; for 2h; Hydrolysis;	94%

8,8-Dimethoxy-2,7-dimethylocta-2,4,6-trien-1-al → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With hydrogenchloride In acetone for 0.166667h; Ambient temperature;	92%

(2E,4E,6E)-1,1,8,8-tetramethoxy-2,7-dimethylocta-2,4,6-triene (128759-95-5) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With acetic acid In tetrahydrofuran at 45℃; for 3h;	90%

1,8-diethoxy-1,3,6,8-tetramethoxy-2,7-dimethyl-4-octene → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With sodium acetate; acetic acid In water at 95℃;	85%

methyl prop-1-enyl ether (7319-16-6) + 1,1,4,4-tetramethoxy-2-butene (5370-08-1) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
Stage #1: methyl prop-1-enyl ether; 1,1,4,4-tetramethoxy-2-butene With iron(III) chloride In toluene at 25℃; for 6h; Stage #2: With sulfuric acid; water In toluene at 80℃; for 5 - 8h; Stage #3: With water; sodium hydrogencarbonate In toluene at 80 - 85℃; for 3 - 4h; Product distribution / selectivity;	83.6%

(E)-3-iodo-2-methylprop-2-enal (106484-89-3) + (2E,4E)-2-methyl-5-(tributylstannyl)-2,4-pentadien-1-al → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With triphenyl-arsane; tris-(dibenzylideneacetone)dipalladium(0) In 1-methyl-pyrrolidin-2-one at 25℃;	80%

(2E,4E,6E)-2,6-dimethylocta-2,4,6-triene-1,8-diol (113951-62-5) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With manganese(IV) oxide In acetone at 0 - 20℃;	73%
With manganese(IV) oxide In acetone at 0℃;	58%
With manganese(IV) oxide In acetone at 0℃;	26%

hydrogen bis(oxalato)borate + methyl (Z)-prop-1-enyl ether (4188-68-5) + trans-butenedial bis-(dimethyl acetal) (6068-62-8) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In water	67%

2,7-dimethyl-2,4,6-octatrienedial → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With p-toluene sulfinic acid In 1,4-dioxane for 0.25h; Heating / reflux;	66%
With toluene-4-sulfonic acid In 1,4-dioxane for 0.25h; Product distribution / selectivity; Heating / reflux;	66%
With toluene-4-sulfonic acid In 1,4-dioxane for 0.25h; Inert atmosphere; Reflux;	16%

1,1,8,8-tetramethoxy-2,7-dimethyl-2,4,6-octatriene → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With acetic acid In tetrahydrofuran; water at 45 - 54℃; for 3h; Product distribution / selectivity;	58.8%
Multi-step reaction with 2 steps 1: acetic acid / water; tetrahydrofuran / 45 °C / Inert atmosphere 2: toluene-4-sulfonic acid / 1,4-dioxane / 0.25 h / Inert atmosphere; Reflux View Scheme
With acetic acid In tetrahydrofuran; water at 45 - 54℃; for 3.5h;	10.75 g

2,2'-(1,6-Dimethyl-1,3,5-hexatrienylen)bis(5,5-dimethyl-1,3-dioxan) (209615-09-8) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + 7-(5,5-Dimethyl-1,3-dioxan-2-yl)-2,7-dimethyl-2,4,6-octatrienal (80713-45-7)

Conditions	Yield
With hydrogenchloride In methanol; dichloromethane for 0.0333333h; Ambient temperature; Yields of byproduct given;	A n/a B 37%

Pyruvic aldehyde dimethyl acetal (6342-56-9) + tetraethyl (E)-2-butene-1,4-diphosphonate (1112-96-5, 16626-80-5, 56727-14-1) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
Stage #1: Pyruvic aldehyde dimethyl acetal; tetraethyl (E)-2-butene-1,4-diphosphonate With sodium hydride In tetrahydrofuran at 0 - 60℃; for 3h; Inert atmosphere; Cooling with ice; Stage #2: With sulfuric acid In tetrahydrofuran; water at 0 - 50℃; for 2.5h;	35%

2,7-dimethyl-octa-2,6-diene-1,8-diol (29146-49-4) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With manganese(IV) oxide; chloroform

2,7-dimethyl-octa-2t,4c,6t-trienedial (181963-79-1) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With benzene
With iodine; Petroleum ether; benzene

2,7-dimethyl-octa-2t,4c,6t-trienedial (181963-79-1) + benzene (71-43-2) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

1,1,3,6,8,8-hexaethoxy-2,7-dimethyl-oct-4t(?)-ene → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
With 1,4-dioxane; phosphoric acid; hydroquinone at 100℃;
With water; acetic acid; ethyl acetate at 100℃; in Gegenwart von Hydrochinon;

2,7-dimethyl-octa-2,6-diene-1,8-diol (29146-49-4) + chloroform (67-66-3) + manganese (IV)-oxide → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

2,7-dimethyl-octa-2t,4c,6t-trienedial (181963-79-1) + iodine (7553-56-2) + benzene (71-43-2) + petroleum ether → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
mit Licht.Irradiation;

4-chloro-2-methyl-2-buten-1-al neopentyl acetal (62285-88-5) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / Na2S*9H2O / methanol / 10 h / 20 °C 2: 80 percent / urea-hydrogen peroxide; phthalic anhydride / acetonitrile / 1 h / 0 °C 3: 82 percent / KOH / 2-methyl-propan-2-ol; CCl4 / 5 h / 20 °C 4: 94 percent / HCl / tetrahydrofuran / 2 h / 20 °C View Scheme

(E)-4-chloro-2-methylbut-2-enal (26394-25-2) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 75 percent / p-TsOH / benzene / 3 h / Heating 2: 95 percent / Na2S*9H2O / methanol / 10 h / 20 °C 3: 80 percent / urea-hydrogen peroxide; phthalic anhydride / acetonitrile / 1 h / 0 °C 4: 82 percent / KOH / 2-methyl-propan-2-ol; CCl4 / 5 h / 20 °C 5: 94 percent / HCl / tetrahydrofuran / 2 h / 20 °C View Scheme

isoprene epoxide (1838-94-4) + 2-ThNNa*CuCN*C5H4NCH2Li → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions

Yield

Multi-step reaction with 6 steps 1: 30.1 g / CuCl2; LiCl / ethyl acetate / 0.5 h / 80 °C 2: 75 percent / p-TsOH / benzene / 3 h / Heating 3: 95 percent / Na2S*9H2O / methanol / 10 h / 20 °C 4: 80 percent / urea-hydrogen peroxide; phthalic anhydride / acetonitrile / 1 h / 0 °C 5: 82 percent / KOH / 2-methyl-propan-2-ol; CCl4 / 5 h / 20 °C 6: 94 percent / HCl / tetrahydrofuran / 2 h / 20 °C View Scheme

bis(3-formyl-3-methyl-2-propenyl) sulfide dineopentyl diacetal (251291-86-8) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / urea-hydrogen peroxide; phthalic anhydride / acetonitrile / 1 h / 0 °C 2: 82 percent / KOH / 2-methyl-propan-2-ol; CCl4 / 5 h / 20 °C 3: 94 percent / HCl / tetrahydrofuran / 2 h / 20 °C View Scheme

bis(3-formyl-3-methyl-2-propenyl) sulfone dineopentyl diacetal (251291-85-7) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / KOH / 2-methyl-propan-2-ol; CCl4 / 5 h / 20 °C 2: 94 percent / HCl / tetrahydrofuran / 2 h / 20 °C View Scheme

isoprene (78-79-5) + tricarbonyl(η6-1,3,5-cyclooctatriene)chromium(O) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: N-bromosuccinamide; water / 10 h 1.2: NaOH / H2O / 1 h / 20 °C 2.1: 30.1 g / CuCl2; LiCl / ethyl acetate / 0.5 h / 80 °C 3.1: 75 percent / p-TsOH / benzene / 3 h / Heating 4.1: 95 percent / Na2S*9H2O / methanol / 10 h / 20 °C 5.1: 80 percent / urea-hydrogen peroxide; phthalic anhydride / acetonitrile / 1 h / 0 °C 6.1: 82 percent / KOH / 2-methyl-propan-2-ol; CCl4 / 5 h / 20 °C 7.1: 94 percent / HCl / tetrahydrofuran / 2 h / 20 °C View Scheme

methyl (E)-4-bromo-2-methylbut-2-enoate (99968-60-2, 27652-16-0) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper-zinc; tetrahydrofuran / Erwaermen des Produkts mit N-Brom-succinimid und wenig Dibenzoylperoxid in Tetrachlormethan unter Belichtung und Erhitzen des erhaltenen Produkts mit 2,4,6-Trimethyl-pyridin und wenig 2,4-Dimethyl-pyridin 2: lithium alanate; diethyl ether 3: acetone; manganese (IV)-oxide View Scheme

(1E,5E)-1,6-dimethyl-1,6-diformyl-1,5-hexadiene-3-yne (53163-61-4) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Lindlar-catalyst; methanol / Hydrogenation 2: iodine; benzene; petroleum ether View Scheme

2,7-dimethyl-octa-2ξ,4c,6ξ-triene-1,8-diol (113951-62-5) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone; manganese (IV)-oxide / unter Lichtausschluss 2: iodine; benzene; petroleum ether View Scheme

dimethyl (2E,4E,6E)-2,7-dimethylocta-2,4,6-triene-1,8-dioate (84695-32-9) → (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium alanate; diethyl ether 2: acetone; manganese (IV)-oxide View Scheme
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 - -20 °C / Inert atmosphere 2: manganese(IV) oxide; sodium carbonate / acetone / 0 - 25 °C / Inert atmosphere View Scheme

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + 4'-((diphenylphosphinoyl)methylene)-2,2':6',2''-terpyridine (208597-43-7) → C42H34N6

Conditions	Yield
With lithium diisopropyl amide	98%

Br(1-)*C41H48O2PS(1+) + (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) → C54H72O4S2

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 20℃; for 10h;	98%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + (1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol (59057-30-6) + triphenylphosphine (603-35-0) → beta-carotene (7235-40-7)

Conditions	Yield
Stage #1: (1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol; triphenylphosphine With hydrogenchloride In methanol; water at 45℃; for 1h; Stage #2: (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial With 1,2-bis (3-methylimidazolium-1-yl) ethane dihydroxide; sodium carbonate In methanol; water at 20℃; for 3h; Reagent/catalyst; Temperature; Wittig Olefination; Inert atmosphere;	95%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + <5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid → (3S,3'S)-astaxanthin (472-61-7) + (3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione (71772-51-5)

Conditions	Yield
With sodium methylate In methanol at 0 - 25℃; for 4h;	A 94.6% B 4.2 % Chromat.
In various solvent(s) for 20h; Heating;	A 97.7 % Chromat. B 2.1 % Chromat.

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + C19H31O4P → canthaxanthin (514-78-3)

Conditions	Yield
With sodium t-butanolate In dimethyl sulfoxide; toluene at -20℃; for 6h; Reagent/catalyst; Temperature; Solvent;	92.1%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + <(2'E,4'E)-5'-(2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3'-methyl-2',4'-pentadienyl>triphenylphosphonium chloride (83020-78-4) → 3-oxo-12'-apo-ε-caroten-12'-al (143077-43-4)

Conditions	Yield
With sodium methylate In methanol; dichloromethane at -20℃;	92%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + <5-(4'-Hydroxy-2',6',6'-trimethyl-3'-oxo-1',4'-cyclohexadien-1'-yl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid → astacene (34026-74-9, 58769-83-8)

Conditions	Yield
With ethyloxirane	91.3%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + <(2E,4E)-5-<(R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl>-3-methylpenta-2,4-dienyl>-triphenylphosphonium chloride → zeaxanthin (144-68-3, 3309-19-1, 24502-92-9, 29472-68-2, 31272-50-1, 31272-53-4, 57820-80-1, 60046-54-0, 60497-64-5, 60497-65-6, 72002-36-9, 72580-10-0, 100347-92-0, 100347-97-5, 136656-95-6, 136733-98-7, 136733-99-8, 136734-01-5, 136734-02-6)

Conditions	Yield
With ethyloxirane In ethanol for 20h; Heating;	90%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) → diethyl-10,10'-diapocarotene-10,10'-dioate (53163-55-6)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 0.5h;	88%

L-valine (72-18-4) + (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) → C20H28N2O4(2-)*2Na(1+)

Conditions	Yield
With sodium methylate In methanol; toluene Ambient temperature;	87%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + Z-(3,7-dimethylocta-2,6-dienyl)diphenylphosphine oxide (70143-03-2) → (6Z,8E,10E,12E,14E,16E,18Z)-2,6,10,15,19,23-hexamethyl-tetracosa-2,6,8,10,12,14,16,18,22-nonaene (13832-81-0, 53872-51-8, 70191-51-4, 81738-47-8, 81738-48-9, 89064-90-4, 89064-91-5, 89164-53-4) + 2,6,10,15,19,23-hexamethyl-2,6,8,10,12,14,16,18,22-tetracosanonaene (53872-51-8) + (6Z,8E,10E,12E,14E,16E,18E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,8,10,12,14,16,18,22-nonaene (13832-81-0, 53872-51-8, 70191-51-4, 81738-47-8, 81738-48-9, 89064-90-4, 89064-91-5, 89164-53-4)

Conditions	Yield
With n-butyllithium In tetrahydrofuran for 3h; Ambient temperature;	A 86% B n/a C n/a

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + C33H38ClOP → zeaxanthin (144-68-3, 3309-19-1, 24502-92-9, 29472-68-2, 31272-50-1, 31272-53-4, 57820-80-1, 60046-54-0, 60497-64-5, 60497-65-6, 72002-36-9, 72580-10-0, 100347-92-0, 100347-97-5, 136656-95-6, 136733-98-7, 136733-99-8, 136734-01-5, 136734-02-6)

Conditions	Yield
With palladium diacetate In ethanol Heating;	85%

2,7-dimethyl-octa-2t,4c,6t-trienedial (181963-79-1) + (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide → Astaxanthin

Conditions	Yield
Stage #1: 2,7-dimethyl-octa-2t,4c,6t-trienedial; (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial; [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide In 2-(2-methoxyethoxy)ethyl alcohol; dichloromethane at 21℃; for 0.5h; Wittig Reaction; Stage #2: With sodium methylate In methanol; 2-(2-methoxyethoxy)ethyl alcohol; dichloromethane at 0 - 3℃; for 2.5h; Stage #3: With acetic acid In methanol; 2-(2-methoxyethoxy)ethyl alcohol; dichloromethane at 105 - 107℃; for 4h; Product distribution / selectivity;	84%
Stage #1: 2,7-dimethyl-octa-2t,4c,6t-trienedial; (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial; [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide In 2-methoxy-ethanol at 25 - 45℃; for 0.5h; Wittig Reaction; Stage #2: With sodium methylate In methanol; 2-methoxy-ethanol at 25 - 30℃; for 2.16667h; Stage #3: With acetic acid In methanol; 2-methoxy-ethanol at 100℃; for 4h; Product distribution / selectivity;	82.2%
Stage #1: 2,7-dimethyl-octa-2t,4c,6t-trienedial; (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial; [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide In 2-(2-methoxyethoxy)ethyl alcohol at 25 - 80℃; for 0.5h; Wittig Reaction; Stage #2: With sodium methylate In methanol; 2-(2-methoxyethoxy)ethyl alcohol at 25 - 30℃; for 2.5h; Stage #3: With acetic acid In methanol; 2-(2-methoxyethoxy)ethyl alcohol at 100℃; for 4h; Product distribution / selectivity;	75.2%
Stage #1: 2,7-dimethyl-octa-2t,4c,6t-trienedial; (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial; [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide In 1-methoxy-2-propanol at 25 - 80℃; for 0.5h; Wittig Reaction; Stage #2: With sodium methylate In methanol; 1-methoxy-2-propanol at 25 - 30℃; for 2.16667h; Stage #3: With acetic acid In methanol; 1-methoxy-2-propanol at 100℃; for 4h; Product distribution / selectivity;	70.57%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + <(4E)-5-(4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid → (±)-astaxanthin (472-61-7, 7542-45-2, 60760-95-4, 64838-38-6, 71772-51-5, 74601-68-6, 111139-31-2, 111139-32-3, 111139-33-4, 113085-04-4, 113085-05-5, 119478-03-4, 122871-99-2, 130467-19-5, 130548-13-9)

Conditions	Yield
With ethyloxirane; water 1.) reflux; 2.) ethanol, reflux, 18 h; (Z->E) isomerisation in heptane;	82.5%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + <5-((R)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid → (3R,3'R)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione (60760-95-4)

Conditions	Yield
	81.2%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + L-phenylalanine (63-91-2) → C28H28N2O4(2-)*2Na(1+)

Conditions	Yield
With sodium methylate In methanol; toluene Ambient temperature;	81%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) → (all-E)-8-hydroxy-2,7-dimethylocta-2,4,6-trienal (76686-46-9)

Conditions	Yield
With sodium tetrahydroborate In ethanol	80%
With sodium tetrahydroborate In methanol

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + benzo[d][1,3]dithiol-2-yltriphenylphosphonium tetrafluoroborate → (2E,4E,6E)-8-Benzo[1,3]dithiol-2-ylidene-2,7-dimethyl-octa-2,4,6-trienal (121881-08-1)

Conditions	Yield
With sodium hydroxide In dichloromethane	80%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2)

Conditions	Yield
Stage #1: (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial; [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide With ethyloxirane In isopropyl alcohol for 18h; Heating / reflux; Stage #2: In dichloromethane Heating / reflux;	80%
In various solvent(s) at 63℃; for 20h; Condensation; Wittig reaction;	55%
With ethyloxirane at 63℃; for 20h;	54.7%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide (63184-93-0) → canthaxanthin (514-78-3)

Conditions	Yield
With sodium methylate In methanol; dichloromethane at -10℃; for 1h;	78%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + neryltriphenylphosphonium bromide (60346-00-1) → (6Z,8E,10E,12E,14E,16E,18Z)-2,6,10,15,19,23-hexamethyl-tetracosa-2,6,8,10,12,14,16,18,22-nonaene (13832-81-0, 53872-51-8, 70191-51-4, 81738-47-8, 81738-48-9, 89064-90-4, 89064-91-5, 89164-53-4) + (6Z,8Z,10E,12E,14E,16Z,18Z)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,8,10,12,14,16,18,22-nonaene (13832-81-0, 53872-51-8, 70191-51-4, 81738-47-8, 81738-48-9, 89064-90-4, 89064-91-5, 89164-53-4)

Conditions	Yield
In tetrahydrofuran at 0℃;	A 77% B n/a
In tetrahydrofuran at 0℃;

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + (all-E)-5-<(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl>-3-methyl-2,4-pentadienyltriphenylphosphonium bromide → (all-E)-(3R)-3-hydroxy-12'-apo-β-caroten-12'-al (62742-02-3)

Conditions	Yield
With sodium hydride In dichloromethane at 20℃; for 12h;	77%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide → 3,3'-dihydroxy-β,β-carotene-4,4'-dione (7542-45-2) + semi-astacene (106776-90-3) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
Stage #1: (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial; [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide With sodium methylate In methanol; dichloromethane at -5℃; for 19.6 - 20.5h; Stage #2: With acetic acid In methanol; dichloromethane Product distribution / selectivity;	A 75.8% B n/a C n/a

Upstream product

• 62285-88-5 4-chloro-2-methyl-2-buten-1-al neopentyl acetal 
• 78-79-5 isoprene 
• 36551-27-6 1,1,3-triethoxy-2-methyl-butane 
• 100624-48-4 1,1,8,8-tetraethoxy-2,7-dimethyl-octa-2,4,6-triene 
• 39501-93-4 1-ethoxy-2-methyl-buta-1,3-diene 
• 7319-16-6 methyl prop-1-enyl ether 
• 5370-08-1 1,1,4,4-tetramethoxy-2-butene 
• 29146-49-4 2,7-dimethyl-octa-2,6-diene-1,8-diol 
• 86043-79-0 2,7-dimethyl-octa-2,6-dienedioic acid dimethyl ester 
• 90031-29-1 1,8-dimethoxy-1,3,6,8-tetramethoxy-2,7-dimethyl-4-octene 
• 5056-17-7 2,7-dimethyl-2,4,6-octanetriene-1,8-dialdehyde 
• 211677-08-6 tetraethyl trans-2-butenyl-1,4-bisphosphonate 
• 136949-10-5 (2E,4E)-Ethyl 6,6-Dimethoxy-2-methylhexa-2,4-dienoate 
• 64768-01-0 diethyl 2,7-dimethyl-2(E),4(E),6(E)-octatriene-1,8-dioate 

Downstream Products

• 1638-05-7 β-Apo-12'-carotenal 
• 72523-68-3 (S)-2,7,11-trimethyl-13-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8,10,12-tridecahexaen-1-al 
• 50299-51-9 Phoeniconon 
• 5794-15-0 Astacindiacetat 
• 39668-26-3 (all-E,2R,2'R)-β,β-Carotin-2,2'-diol 
• 4418-72-8 3-hydroxy-β,β-caroten-4,4'-dione 
• 65861-49-6 4-oxo-β-apo-12’-carotenal 
• 80713-42-4 rac-3-Hydroxy-4-oxo-12'-apo-β-carotin-12'-al 
• 6399-46-8 3-Hydroxy-2,3-didehydro-β,β-carotin-4-on 
• 80713-38-8 rac-3,3'-Dihydroxy-2,3-didehydro-β,β-carotin-4,4'-dion 
• 4339-77-9 3-hydroxy-β,β-caroten-4-one 
• 72843-12-0 (3S)-Hydroxyechinenon 
• 72843-13-1 (3S)-3-Hydroxy-β,β-carotin-4,4'-dion 
• 71772-51-5 (3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione 

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