555-10-2

Basic information

• Product Name: beta-Phellandrene
• Synonyms: beta-Phellandrene; 2-p-Menthadiene; 3-Isopropyl-6-methylene-1-cyclohexene; 3-Methylene-6-(1-methylethyl)cyclohexene; 4-Isopropyl-1-methylene-2-cyclohexene; Cyclohexene, 3-methylene-6-(1-methylethyl)-; HSDB 4080; NSC 53044; PHELLANDRENE, BETA; p-Mentha-1(7),2-diene; 3-methylidene-6-(propan-2-yl)cyclohexene; (6S)-3-methylidene-6-(propan-2-yl)cyclohexene
• CAS NO: 555-10-2
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 0
• EINECS: 209-081-9
• Mol File: 555-10-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 175°Cat760mmHg
• Flash Point: 44°C
• Appearance: /
• Density: 0.82g/cm³
• Vapor Pressure: 1.57mmHg at 25°C
• Refractive Index: 1.466
• CAS DataBase Reference: beta-Phellandrene(CAS DataBase Reference)
• NIST Chemistry Reference: beta-Phellandrene(555-10-2)
• EPA Substance Registry System: beta-Phellandrene(555-10-2)

Safety Data

• Hazardous Substances Data: 555-10-2(Hazardous Substances Data)

Usage

General Description

Beta-phellandrene is a monoterpene chemical compound found in a variety of essential oils, including those derived from eucalyptus, mint, and pine. It is known for its fresh, minty, and somewhat citrusy aroma, making it a popular ingredient in perfumes and fragrances. Beyond its aromatic qualities, beta-phellandrene also possesses therapeutic properties, such as anti-inflammatory, antibacterial, and antifungal effects. Additionally, it has been studied for its potential use in insect repellents and as a flavoring agent in the food industry. Overall, beta-phellandrene is a versatile and multifaceted compound with a range of applications in both the fragrance and health industries.

InChI:InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3/t10-/m0/s1

Synthetic route

cryptone (2158-59-0, 2158-61-4, 100295-52-1, 500-02-7) + Methyltriphenylphosphonium bromide (1779-49-3) → beta-phellandrene (555-10-2)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran; diethyl ether at 20℃; for 0.166667h; Stage #2: cryptone In tetrahydrofuran; diethyl ether for 0.333333h; Wittig reaction;	69%

1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) → p-mentha-1,5-diene (99-83-2) + 3,8-p-Menthadien (586-67-4) + crithmene (99-85-4) + beta-phellandrene (555-10-2) + (+/-)-2,4-p-menthadiene (586-68-5) + isoterpinolene (586-63-0)

Conditions	Yield
With aluminum oxide at 250℃; Equilibrium constant; gas phase isomerization;

isoterpinolene (586-63-0) → beta-phellandrene (555-10-2)

Conditions	Yield
at 560℃; Thermodynamic data; ΔH(react.), ΔS(react);

methanol (67-56-1) + piperitol (491-04-3) → p-mentha-1,5-diene (99-83-2) + beta-phellandrene (555-10-2) + (4-isopropyl-1-methyl-2-cyclohexenyl) methyl ether (94281-61-5) + cis-(6-isopropyl-3-methyl-2-cyclohexenyl) methyl ether

Conditions	Yield
With cerium(III) chloride for 0.5h; Heating; Further byproducts given;

methanol (67-56-1) + piperitol (491-04-3) → beta-phellandrene (555-10-2) + (4-isopropyl-1-methyl-2-cyclohexenyl) methyl ether (94281-61-5) + cis-(6-isopropyl-3-methyl-2-cyclohexenyl) methyl ether + trans-(6-isopropyl-3-methyl-2-cyclohexenyl) methyl ether

Conditions	Yield
With cerium(III) chloride for 0.5h; Heating; Further byproducts given;

ethanol (64-17-5) + piperitol (491-04-3) → beta-phellandrene (555-10-2) + (4-isopropyl-1-methyl-2-cyclohexenyl) ethyl ether (54982-74-0) + cis-(6-isopropyl-3-methyl-2-cyclohexenyl) ethyl ether (54982-75-1, 54982-77-3) + trans-(6-isopropyl-3-methyl-2-cyclohexenyl) ethyl ether (54982-75-1, 54982-77-3)

Conditions	Yield
With cerium(III) chloride for 0.5h; Heating; Further byproducts given;

piperitol (491-04-3) → p-mentha-1,5-diene (99-83-2) + 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + beta-phellandrene (555-10-2)

Conditions	Yield
With cerium(III) chloride In isopropyl alcohol for 1h; Heating;

piperitol (491-04-3) → p-mentha-1,5-diene (99-83-2) + beta-phellandrene (555-10-2)

Conditions	Yield
With cerium(III) chloride In tert-butyl alcohol for 1h; Heating;

piperitol (491-04-3) → 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + beta-phellandrene (555-10-2) + (4-isopropyl-1-methyl-2-cyclohexenyl) n-propyl ether + (3S,4R)-4-Isopropyl-1-methyl-3-propoxy-cyclohexene

Conditions	Yield
With cerium(III) chloride In propan-1-ol for 0.5h; Heating; Further byproducts given;

cryptone (2158-59-0, 2158-61-4, 100295-52-1, 500-02-7) + dimethyl sulfoxide (67-68-5) → beta-phellandrene (555-10-2)

Conditions	Yield
Stage #1: dimethyl sulfoxide With sodium hydride for 3h; Metallation; Stage #2: With Methyltriphenylphosphonium bromide In dimethyl sulfoxide ylidation; Stage #3: cryptone In dimethyl sulfoxide Wittig's reaction;	22.7 g

Geraniol (106-24-1) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + 7-methyl-3-methene-1,6-octadiene (123-35-3) + 3,7-Dimethyl-octa-1,3,6-trien (13877-91-3) + beta-phellandrene (555-10-2) + (R)-5-isopropyl-2-methylcyclohexa-1,3-diene (4221-98-1) + 3,7-dimethyl-1,3,7-octatriene

Conditions	Yield
With boron pentasil zeolite at 220℃; under 60.006 Torr; for 2h; Gas phase;

Geraniol (106-24-1) → 7-methyl-3-methene-1,6-octadiene (123-35-3) + beta-phellandrene (555-10-2) + (R)-5-isopropyl-2-methylcyclohexa-1,3-diene (4221-98-1)

Conditions	Yield
With H-ZSM5 zeolite at 220℃; under 60.006 Torr; for 2h; Gas phase;

geranyl diphosphate (763-10-0) → Beta-pinene (177698-19-0) + Pinene (80-56-8, 177698-18-9) + beta-phellandrene (555-10-2) + (-)-(S)-limonene (5989-54-8)

Conditions	Yield
With Mentha spicata S-limonene synthase, mutant (N345A/L423A/S454A); magnesium chloride; D,L-dithiothreitol In hexane; glycerol at 37℃; for 0.666667h; pH=7; Mechanism; Reagent/catalyst; Enzymatic reaction; chemoselective reaction;	A 47.07 %Chromat. B 21.68 %Chromat. C 17.72 %Chromat. D 9.19 %Chromat.
With Mentha spicata S-limonene synthase, mutant N345S; magnesium chloride; D,L-dithiothreitol In hexane; glycerol at 37℃; for 0.666667h; pH=7; Mechanism; Enzymatic reaction; chemoselective reaction;	A 6.69 %Chromat. B 7.12 %Chromat. C 15.47 %Chromat. D 69.84 %Chromat.

geranyl diphosphate (763-10-0) → Beta-pinene (177698-19-0) + Pinene (80-56-8, 177698-18-9) + sabinene (2009-00-9, 10408-16-9, 15826-80-9, 3387-41-5) + beta-phellandrene (555-10-2) + (-)-(S)-limonene (5989-54-8)

Conditions	Yield
With Mentha spicata S-limonene synthase, (N345A/L423A/S454G) mutant; magnesium chloride; D,L-dithiothreitol In hexane; glycerol at 37℃; for 0.666667h; pH=7; Mechanism; Enzymatic reaction; chemoselective reaction;	A 52.7 %Chromat. B 9.84 %Chromat. C 5.29 %Chromat. D 17.9 %Chromat. E 13.37 %Chromat.

geranyl diphosphate (763-10-0) → p-mentha-1,5-diene (99-83-2) + Pinene (80-56-8, 177698-18-9) + beta-phellandrene (555-10-2) + (-)-(S)-limonene (5989-54-8)

Conditions	Yield
With Mentha spicata S-limonene synthase, mutant N345I; magnesium chloride; D,L-dithiothreitol In hexane; glycerol at 37℃; for 0.666667h; pH=7; Mechanism; Enzymatic reaction; chemoselective reaction;	A 29.47 %Chromat. B 11.79 %Chromat. C 39.4 %Chromat. D 18.48 %Chromat.

4-isopropyl-cyclohexanone (5432-85-9) → beta-phellandrene (555-10-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.08 h / -78 °C / Inert atmosphere 2.1: palladium diacetate; oxygen / dimethyl sulfoxide / 20 h / 20 °C / Inert atmosphere 2.2: 0.03 h / 0 - 20 °C / Inert atmosphere View Scheme

methyl-triphenylphosphonium iodide (2065-66-9) + (4-isopropylcyclohex-1-enyloxy)trimethylsilane (74173-20-9) → beta-phellandrene (555-10-2)

Conditions	Yield
Stage #1: (4-isopropylcyclohex-1-enyloxy)trimethylsilane With oxygen; palladium diacetate In dimethyl sulfoxide at 20℃; for 20h; Inert atmosphere; Stage #2: methyl-triphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 0.025h; Inert atmosphere;	2.26 g

beta-phellandrene (555-10-2) → (1RS,2SR,3SR,4SR)-1,2,3,7-tetrabromo-p-menthane (3247-45-8, 52020-22-1)

Conditions	Yield
With bromine In acetic acid

beta-phellandrene (555-10-2) → (+/-)-(1R,2R,3R,4R)-1,2,3-Tribromo-p-menthan (51941-37-8, 52020-23-2)

Conditions	Yield
(i) aq. HBr, AcOH, (ii) Br2; Multistep reaction;

beta-phellandrene (555-10-2) → p-mentha-1,5-diene (99-83-2) + 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + 3,8-p-Menthadien (586-67-4) + crithmene (99-85-4) + (+/-)-2,4-p-menthadiene (586-68-5) + isoterpinolene (586-63-0)

Conditions	Yield
With aluminum oxide at 250℃; Product distribution; gas phase isomerization;	A 3.1 % Chromat. B 44.9 % Chromat. C 4.4 % Chromat. D 16.4 % Chromat. E 4.6 % Chromat. F 21.6 % Chromat.

beta-phellandrene (555-10-2) → 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5)

Conditions	Yield
With aluminum oxide at 250℃; Equilibrium constant; gas phase isomerization;

beta-phellandrene (555-10-2) + isopentyl nitrite (110-46-3) + alcoholic hydrogen chloride → α nitrosochloride + β nitrosochloride

Conditions	Yield
d-β-phellandrene;

beta-phellandrene (555-10-2) + KMnO4 → 2-hydroxy-3-isopropyl-adipic acid

Conditions	Yield
dextrorotatory form;

beta-phellandrene (555-10-2) + copper → Menthane (99-82-1, 1678-82-6, 6069-98-3, 129939-70-4, 129939-71-5) + 4-methylisopropylbenzene (99-87-6)

Conditions	Yield
at 300℃; dextrorotatory β-phellandrene;

hydrogenchloride (7647-01-0) + beta-phellandrene (555-10-2) → 1,4-dichloro-trans-p-menthane (25570-95-0)

Conditions	Yield
d-β-phellandrene;

beta-phellandrene (555-10-2) + moist oxygen → cryptone (2158-59-0, 2158-61-4, 100295-52-1, 500-02-7)

Conditions	Yield
Sonnenlicht; dextrorotatory form;

beta-phellandrene (555-10-2) → diphellandrene

Conditions	Yield
at 140 - 150℃; im geschlossenen Rohr; dextrorotatory form;

beta-phellandrene (555-10-2) → diterpene C20H32

Conditions	Yield
beim Erhitzen im Einschlussrohr; d-β-phellandrene;

beta-phellandrene (555-10-2) + isoprene (78-79-5) → sesquiterpene C15H24

Conditions	Yield
beim Erhitzen im Einschlussrohr; d-β-phellandrene;

sodium tetrachloropalladate + beta-phellandrene (555-10-2) → [PdCl(C6H7(CH3)(CH(CH3)2))]2

Conditions	Yield
In methanol byproducts: C6H4(CH3)(CH(CH3)2), C6H6(CH3)(CH(CH3)2), NaCl; 50-60°C, further by-product: HCl; total yield of cis and trans: 90%;

sodium tetrachloropalladate + beta-phellandrene (555-10-2) → [PdCl(C6H7(CH(CH3)2)(OCH3)CH2)]2

Conditions	Yield
In methanol 0°C; elem. anal.;

Upstream product

• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 586-63-0 isoterpinolene 
• 67-56-1 methanol 
• 491-04-3 piperitol 
• 64-17-5 ethanol 
• 2158-59-0 cryptone 
• 67-68-5 dimethyl sulfoxide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 106-24-1 Geraniol 
• 763-10-0 geranyl diphosphate 
• 5432-85-9 4-isopropyl-cyclohexanone 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 74173-20-9 (4-isopropylcyclohex-1-enyloxy)trimethylsilane 

Downstream Products

• 3247-45-8 (1RS,2SR,3SR,4SR)-1,2,3,7-tetrabromo-p-menthane 
• 99-83-2 p-mentha-1,5-diene 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 586-67-4 3,8-p-Menthadien 
• 99-85-4 crithmene 
• 586-68-5 (+/-)-2,4-p-menthadiene 
• 586-63-0 isoterpinolene 
• 99-82-1 Menthane 
• 99-87-6 4-methylisopropylbenzene 
• 25570-95-0 1,4-dichloro-trans-p-menthane 
• 2158-59-0 cryptone 

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